KR20130135424A - Novel potassium organo-1h-1,2,3-triazol-4-yltrifluoroborate derivatives and method for producing the same - Google Patents

Abstract

The present invention relates to a novel potassium organo-1H-1,2,3-triazole-4-yltrifluoroborate derivative and a manufacturing method thereof. The novel potassium organo-1H-1,2,3- triazole-4-yltrifluoroborate derivative according to the present invention can be usefully used in the manufacture of various kinds of organo 1,2,3-triazole through a general carbon-carbon coupling reaction utilizing a metallic catalyst such as Suzuki-Miyaura coupling, and can be applied to an organic combination reaction, an optical organic material manufacture, medicine production, a medical diagnosis material, a biocompatible material and a bioactive natural material. The manufacturing method for the potassium organo-1H-1,2,3-triazole-4-yltrifluoroborate derivative according to the present invention can manufacture the stable potassium organo-1H-1,2,3-triazole-4-yltrifluoroborate derivative with a single reaction. Accordingly, a manufacturing process is fast, convenient, efficient and economic.

Description

NOVEL POTASSIUM ORGANO-1H-1,2,3-TRIAZOL-4-YLTRIFLUOROBORATE DERIVATIVES AND METHOD This invention relates to novel potassium organo-1H-1,2,3-triazol- FOR PRODUCING THE SAME}

The present invention relates to a novel potassium organo- 1H -1,2,3-triazol-4-yl trifluoro borate derivative and a process for preparing the same. More specifically, 1,2,3-triazole derivatives relates to a new available for the production of potassium organo -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate derivative and a method of manufacturing the same.

Recently, organo-1,2,3-triazole compounds, which are widely used in the fields of organic chemistry, pharmaceutical chemistry and biomaterials, have a fast reaction rate, a mild reaction condition and a high yield , It is an important compound that has been widely used in the field of drug development through the use of combinatorial chemistry and diversity-oriented synthesis, development of medical diagnostic materials, and development of bio-conjugated new materials with high stability.

Despite such availability, however, the diversity of 1,2,3-triazole derivatives has been severely limited in the types of chemical manufacture or sale of the azide compounds and terminal alkanes used.

Recently, in the field of chemistry, a carbon-carbon bonding method using various kinds of palladium (Pd) catalysts is widely used in organic chemistry, medical chemical and chemical materials research. Particularly, the carbon-carbon bond reaction using the organic boron compound is less toxic than the organozinc, organotin, or organic magnesium (Grignard reagent) As a compound it has the advantage of being less dangerous to the human body. In addition, it has the advantage of being more stable than conventional reactions such as using water for reaction conditions, and being easy to apply in various fields (synthesis of natural materials, medicinal chemistry, material chemistry, etc.).

Particularly, in recent years, the use of potassium organotrifluoroborate, which is a kind of organic boron compounds, is increasing. However, up to now, there has been a difficulty in developing an economical method for securing the diversity of the terminal alkane in various production of the organo 1,2,3-triazole compound.

Patent No. 10-1073510

The present invention to solve the above problems relates to novel potassium organo -1 H -1,2,3- triazol-4-yl-trifluoro-borate (Potassium Organo-1 H -1,2,3- triazol -4-yltrifluoroborate) derivatives.

Another object of the present invention is to provide a method for producing potassium alkanoyl-1 H -1, which is capable of reacting potassium ethynyltrifluoroborate with various azide derivatives without limitation of terminal alkyne, , 2,3-triazol-4-yl trifluorofluoroborate derivative. In addition, it has been found that by using a carbon-carbon bond reaction using a palladium catalyst using a potassium organo- 1H -1,2,3-triazol-4-yl trifluoro borate derivative as an efficient and economical organo 1,2 , And a process for producing a 3-triazole compound.

In order to solve the above-mentioned problems, the present invention provides a potassium organo- 1H -1,2,3-triazol-4-yl trifluoroperate derivative represented by the following Chemical Formula 1.

[Formula 1]

(In the formula 1,

R ¹ is a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ Alkyl ether group,

(In the formula 1,

R ¹ is a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ Alkyl ether group,

기 (Ar은 페닐, 바이페닐, 나프틸, 펜옥시페닐, 피리딜, 퓨라닐 및 티오페닐로 이루어진 군으로부터 선택되는 어느 하나 이상이고, R²는 C₁-C₈ 알킬기, C₁-C₄ 알킬옥시기, C₁-C₄ 알킬티오옥시기, C₆-C₁₂ 아릴옥시기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬옥시기, 니트로기(-NO₂), 시안기(-CN), 불소, 염소, 브롬, 요오드, 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, m은 0 내지 5의 정수이고, n은 1 내지 4의 정수임),

Group (Ar represents at least one selected from the group consisting of phenyl, biphenyl, naphthyl, phenoxy, phenyl, pyridyl, furanyl and thiophenyl, R ² is C ₁ -C ₈ alkyl, C ₁ -C ₄ A C ₁ -C ₄ alkylthio group, a C ₆ -C ₁₂ aryloxy group, a C ₁ -C ₄ alkyl group substituted with at least one halogen, a C ₁ -C ₄ alkyloxy group substituted with at least one halogen , Nitro group (-NO ₂ ), cyano group (-CN), fluorine, chlorine, bromine, iodine, and hydrogen, m is an integer of 0 to 5, 4 < / RTI >

기 (R³은 C₁-C₈ 알킬기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, p는 1 내지 5의 정수임), 및

(Wherein R ³ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group and hydrogen, p is an integer of 1 to 5), and

기 (R⁴는 C₁-C₈ 알킬기, 페닐기, 디메틸아민기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, q는 1 내지 5의 정수임)로 이루어진 군으로부터 선택되는 어느 하나 이상이다.)

(Wherein R ⁴ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group, a phenyl group, a dimethylamine group and hydrogen, and q is an integer of 1 to 5).

The present invention also relates to a process for the preparation of a potassium organo- 1H -1,2,3-triazole-1, 2-dicarboxylic acid according to claim 1, which comprises reacting potassium ethynyltrifluoroborate, sodium azide, 4-yl trifluoroborate derivative.

In one embodiment of the present invention, the preparation method may be represented by the following Scheme 1.

 [Reaction Scheme 1]

(In the above Reaction Scheme 1,

기 (Ar은 페닐, 바이페닐, 나프틸, 펜옥시페닐, 피리딜, 퓨라닐 및 티오페닐로 이루어진 군으로부터 선택되는 어느 하나 이상이고, R²는 C₁-C₈ 알킬기, C₁-C₄ 알킬옥시기, C₁-C₄ 알킬티오옥시기, C₆-C₁₂ 아릴옥시기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬옥시기, 니트로기(-NO₂), 시안기(-CN), 불소, 염소, 브롬, 요오드, 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, m은 0 내지 5의 정수이고, n은 1 내지 4의 정수임), R ¹ is a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ Alkyl ether group,

Group (Ar represents at least one selected from the group consisting of phenyl, biphenyl, naphthyl, phenoxy, phenyl, pyridyl, furanyl and thiophenyl, R ² is C ₁ -C ₈ alkyl, C ₁ -C ₄ A C ₁ -C ₄ alkylthio group, a C ₆ -C ₁₂ aryloxy group, a C ₁ -C ₄ alkyl group substituted with at least one halogen, a C ₁ -C ₄ alkyloxy group substituted with at least one halogen , Nitro group (-NO ₂ ), cyano group (-CN), fluorine, chlorine, bromine, iodine, and hydrogen, m is an integer of 0 to 5, 4 < / RTI >

기 (R³은 C₁-C₈ 알킬기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, p는 1 내지 5의 정수임),

(Wherein R ³ is any one or more selected from the group consisting of C ₁ -C ₈ alkyl groups and hydrogen, and p is an integer of 1 to 5)

기 (R⁴는 C₁-C₈ 알킬기, 페닐기, 디메틸아민기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, q는 1 내지 5의 정수임)로 이루어진 군으로부터 선택되는 어느 하나 이상이고,

(Wherein R ⁴ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group, a phenyl group, a dimethylamine group and hydrogen, and q is an integer of 1 to 5)

X is a halogen element.)

In one embodiment of the present invention, the production method may be one in which one or more members selected from the group consisting of a ligand, an additive and an inorganic salt are reacted together.

In one embodiment of the present invention, the catalyst may be a copper halide catalyst.

In one embodiment of the present invention, the copper halide catalyst is selected from the group consisting of copper iodide (CuI), copper bromide (CuBr), copper bromide dimethyl sulfide complex (CuBr.DMS), copper oxide (Cu ₂ O), copper sulfate ≪ _{RTI ID = 0.0} > CuSO4). ≪ / RTI >

In one embodiment of the present invention, the catalyst may be 0.01 to 0.2 equivalents based on potassium ethinyl trifluoroborate.

In one embodiment of the present invention, the halide compound may be 1.0 to 1.5 equivalents based on the potassium ethynyl trifluoroborate derivative.

In one embodiment of the present invention, the ligands are N, N '- may be one of dimethyl ethylene diamine and N, N'- dimethyl-cyclohexane-1,2-diamine or higher.

In one embodiment of the present invention, the ligand may be 0.01 to 0.5 equivalents based on potassium ethinyl trifluoroborate.

In one embodiment of the present invention, the additive may be sodium ascorbate.

In one embodiment of the present invention, the additive may be 0.01 to 0.5 equivalents based on potassium ethinyl trifluoroborate.

In one embodiment of the present invention, the inorganic salt may be at least one selected from the group consisting of potassium carbonate (K ₂ CO ₃ ), sodium carbonate (Na ₂ CO ₃ ), and cesium carbonate (Cs ₂ CO ₃ ).

In one embodiment of the present invention, the inorganic salt may be 0.1 to 2.0 equivalents based on potassium ethinyl trifluoroborate.

In one embodiment of the present invention, the reaction is carried out in one or more solvents selected from the group consisting of N, N- dimethylformamide (DMF), dimethylsulfoxide (DMSO), methanol (MeOH) Lt; / RTI >

In one embodiment of the present invention,

To 150 < 0 > C for 10 minutes to 48 hours.

In addition, the present invention includes a step of performing a carbon-carbon bond reaction, a substitution reaction or an addition reaction using the above potassium organo- 1H -1,2,3-triazol-4-yl trifluoro borate derivative as a starting material Triazole derivative of formula < RTI ID = 0.0 > (I) < / RTI >

In one embodiment of the present invention, the carbon-carbon bond reaction may be performed under a palladium catalyst.

In one embodiment of the present invention, the substitution reaction or the addition reaction may be conducted under a rhodium catalyst.

The novel potassium organo-1 H -1,2,3-triazol-4-yl trifluoro borate derivative according to the present invention can be produced by reacting a metal catalyst such as Suzuki-Miyaura Coupling Reaction The present invention can be used for the production of various kinds of organo-1,2,3-triazole through the general carbon-carbon bond reaction utilized, It can be used variously in the whole synthesis field of biojoint materials and physiologically active natural products. Further, according to the manufacturing method of the potassium organo -1 H -1,2,3- triazol-4-yl tree borate derivative fluoro according to the present invention, stable potassium organo -1 H -1,2,3- Triazol-4-yltrifluoroborate derivatives can be prepared by a single reaction, and the production process is very fast, convenient, efficient and economical.

Hereinafter, preferred embodiments of the present invention will be described in detail in order to facilitate the present invention by those skilled in the art.

The term "C ₁ -C ₈ alkyl group" means a straight or branched, substituted or unsubstituted alkyl group having from 1 to 8 carbon atoms. The alkyl group is preferably a methyl, ethyl, ethenyl, ethynyl, n-propyl, isopropyl, n-butyl, Hexyl, n-heptyl, n-octyl and the like, and more specifically methyl, n-pentyl or isopropyl, but is not limited thereto.

The term "C ₁ -C ₄ alkyloxy group" refers to an alkyl-O- group in which the alkyl may be a straight or branched, saturated or unsaturated, substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms. For example, C ₁ -C ₄ The alkyloxy group may be methoxy, but is not limited thereto. Further, the alkyloxy group containing a substituted alkyl group may be fluorine-substituted methoxy, and may be specifically -OCF ₃ , but is not limited thereto.

The term "C ₆ -C ₁₂ cycloalkyl group" refers to an alkyl group having cyclohexyl, cyclopentyl, cyclopropyl, and the alkyl may be a straight or branched chain alkyl group having from 1 to 6 carbon atoms. More specifically, the C ₆ -C ₁₂ cycloalkyl group may be a cyclohexyl group, but is not limited thereto.

The term "C ₆ -C ₁₅ arylalkyl group" refers to a substituted or unsubstituted C ₆ -C ₁₅ Aromatic hydrocarbons such as, but not limited to, phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, and the like.

The term "C ₂ -C ₉ alkyl ether group" may be a straight or branched, saturated or unsaturated, substituted or unsubstituted alkyl group comprising from 2 to 9 carbon atoms and an ether group.

The present invention provides a novel potassium organo- 1H -1,2,3-triazol-4-yl trifluorafluoroborate derivative represented by the following formula (1).

[Formula 1]

(In the formula 1,

기 (Ar은 페닐 (

), 바이페닐 (

), 나프틸 (

), 펜옥시페닐 (

), 피리딜 (

), 퓨라닐 (

) 및 티오페닐 (

)로 이루어진 군으로부터 선택되는 어느 하나 이상이고, R²는 C₁-C₈ 알킬기, C₁-C₄ 알킬옥시기, C₁-C₄ 알킬티오옥시기, C₆-C₁₂ 아릴옥시기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬옥시기, 니트로기(-NO₂), 시안기(-CN), 불소, 염소, 브롬, 요오드, 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, m은 0 내지 5의 정수이고, n은 1 내지 4의 정수임),

기 (R³은 C₁-C₈ 알킬기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, p는 1 내지 5의 정수임),

기 (R⁴는 C₁-C₈ 알킬기, 페닐기, 디메틸아민기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, q는 1 내지 5의 정수임)로 이루어진 군으로부터 선택되는 어느 하나 이상이다.)R ¹ represents a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ alkyl ether group,

Group (Ar is phenyl (

), Biphenyl (

), Naphthyl (

), Phenoxyphenyl (

), Pyridyl (

), Furanyl (

) And thiophenyl (

), R ² is at least one selected from the group consisting of a C ₁ -C ₈ alkyl group, a C ₁ -C ₄ alkyloxy group, a C ₁ -C ₄ alkylthiooxy group, a C ₆ -C ₁₂ aryloxy group, C ₁ -C ₄ alkyl substituted with one or more halogens, C ₁ -C ₄ alkyloxy substituted with one or more halogens, nitro (-NO ₂ ), cyano (-CN), fluorine, chlorine, bromine, iodine , And hydrogen, m is an integer of 0 to 5, and n is an integer of 1 to 4,

(Wherein R ³ is any one or more selected from the group consisting of C ₁ -C ₈ alkyl groups and hydrogen, and p is an integer of 1 to 5)

(Wherein R ⁴ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group, a phenyl group, a dimethylamine group and hydrogen, and q is an integer of 1 to 5).

The potassium organo-1 H -1,2,3-triazol-4-yl trifluoro borate derivative is obtained by reacting potassium 1-benzyl- 1H -1,2,3-triazol-4-yl trifluoro borate, potassium 1- (3-phenylpropyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (4-methoxybenzyl) -1 H -1,2, 3-triazol-4-yl-trifluoromethyl borate, potassium 1- (4-methylbenzyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (4-cyano Benzyl) -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (3,5-difluorobenzyl) -1 H -1,2,3-triazole- 4-yl trifluoroborate, potassium 1- (2,6-difluorobenzyl) -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1-ethoxycarbonylmethyl -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1-benzyloxycarbonylmethyl-1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (3-methoxycarbonyl-benzyl) -1 H -1,2 , 1,1 '- (1,4-phenylenebis (methylene)) bis ( 1H -1,2,3-triazole) -4,4 '-yl trifluoromethyl borate, potassium 1- (4-bromobenzyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (4-trifluoromethyl-benzyl ) -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (3-trifluoromethylbenzyl) -1 H -1,2,3-triazol- trifluoroacetic borate, potassium 1- (4-nitrobenzyl) -1 H -1,2,3- triazol-4-yl-trifluoro-borate, potassium l-allyl -1 H -1,2,3- triazol 1-phenyl-1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (4-methoxyphenyl) -1 H -1 , 2,3-triazol-4-yl-trifluoro-borate, potassium 1- (3-methoxyphenyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (2-methoxyphenyl) -1 H -1,2,3- triazol-4-yl trifluoroacetate Rate, a potassium 1- (4-trifluoromethylphenyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (3-trifluoromethylphenyl) -1 H -1 , 2,3-triazol-4-yl-trifluoro-borate, potassium 1- (4-aminophenyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- ( 4-hydroxyphenyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (3-hydroxyphenyl) -1 H -1,2,3- triazol- 4-trifluoroborate, and 4-yl trifluoroborate. However, the present invention is not limited thereto.

The present invention also relates to a process for the preparation of potassium organo- 1H -1,2,3-triazole according to claim 1, which comprises reacting potassium ethynyltrifluoroborate, sodium azide and a halide compound under catalysis -4-yl trifluoroborate derivative.

) 화합물을 용매에 녹이고 소듐 아자이드 (NaN₃), 촉매, 리간드, 첨가제와 무기염 하에서 반응 후, 용매를 제거하고 정제하여 제조할 수 있다.
Specifically, the compound of Formula 1 is prepared by reacting potassium ethanetrifluoroborate and halide ((

) Is dissolved in a solvent and reacted with sodium azide (NaN ₃ ), a catalyst, a ligand, an additive and an inorganic salt, and then the solvent is removed and purified.

The above production method may be represented by the following reaction formula (1).

 [Reaction Scheme 1]

(In the above Reaction Scheme 1,

기 (Ar은 페닐, 바이페닐, 나프틸, 펜옥시페닐, 피리딜, 퓨라닐 및 티오페닐로 이루어진 군으로부터 선택되는 어느 하나 이상이고, R²는 C₁-C₈ 알킬기, C₁-C₄ 알킬옥시기, C₁-C₄ 알킬티오옥시기, C₆-C₁₂ 아릴옥시기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬옥시기, 니트로기(-NO₂), 시안기(-CN), 불소, 염소, 브롬, 요오드, 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, m은 0 내지 5의 정수이고, n은 1 내지 4의 정수임), R ¹ represents a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ alkyl ether group,

Group (Ar represents at least one selected from the group consisting of phenyl, biphenyl, naphthyl, phenoxy, phenyl, pyridyl, furanyl and thiophenyl, R ² is C ₁ -C ₈ alkyl, C ₁ -C ₄ A C ₁ -C ₄ alkylthio group, a C ₆ -C ₁₂ aryloxy group, a C ₁ -C ₄ alkyl group substituted with at least one halogen, a C ₁ -C ₄ alkyloxy group substituted with at least one halogen , Nitro group (-NO ₂ ), cyano group (-CN), fluorine, chlorine, bromine, iodine, and hydrogen, m is an integer of 0 to 5, 4 < / RTI >

기 (R³은 C₁-C₈ 알킬기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, p는 1 내지 5의 정수임),

(Wherein R ³ is any one or more selected from the group consisting of C ₁ -C ₈ alkyl groups and hydrogen, and p is an integer of 1 to 5)

기 (R⁴는 C₁-C₈ 알킬기, 페닐기, 디메틸아민기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, q는 1 내지 5의 정수임)로 이루어진 군으로부터 선택되는 어느 하나 이상이고,

(Wherein R ⁴ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group, a phenyl group, a dimethylamine group and hydrogen, and q is an integer of 1 to 5)

X is a halogen element.)

The halogen element may be any one or more of chlorine, bromine and iodine.

The production method of the present invention may be one in which one or more selected from the group consisting of a ligand, an additive and an inorganic salt are reacted together.

Specifically, the preparation method can be represented by the following reaction formula (2).

 [Reaction Scheme 2]

(In the above Reaction Scheme 1,

기 (Ar은 페닐 (

), 바이페닐 (

), 나프틸 (

), 펜옥시페닐 (

), 피리딜 (

), 퓨라닐 (

) 및 티오페닐 (

)로 이루어진 군으로부터 선택되는 어느 하나 이상이고, R²는 C₁-C₈ 알킬기, C₁-C₄ 알킬옥시기, C₁-C₄ 알킬티오옥시기, C₆-C₁₂ 아릴옥시기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬기, 하나 이상의 할로겐이 치환된 C₁-C₄ 알킬옥시기, 니트로기(-NO₂), 시안기(-CN), 불소, 염소, 브롬, 요오드, 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, m은 0 내지 5의 정수이고, n은 1 내지 4의 정수임),

기 (R³은 C₁-C₈ 알킬기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, p는 1 내지 5의 정수임),

기 (R⁴는 C₁-C₈ 알킬기, 페닐기, 디메틸아민기 및 수소로 이루어진 군으로부터 선택되는 어느 하나 이상이며, q는 1 내지 5의 정수임)로 이루어진 군으로부터 선택되는 어느 하나 이상이고, X는 요오드, 브롬 또는 염소이다.)
R ¹ is a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ Alkyl ether group,

Group (Ar is phenyl (

), Biphenyl (

), Naphthyl (

), Phenoxyphenyl (

), Pyridyl (

), Furanyl (

) And thiophenyl (

), R ² is at least one selected from the group consisting of a C ₁ -C ₈ alkyl group, a C ₁ -C ₄ alkyloxy group, a C ₁ -C ₄ alkylthiooxy group, a C ₆ -C ₁₂ aryloxy group, C ₁ -C ₄ alkyl substituted with one or more halogens, C ₁ -C ₄ alkyloxy substituted with one or more halogens, nitro (-NO ₂ ), cyano (-CN), fluorine, chlorine, bromine, iodine , And hydrogen, m is an integer of 0 to 5, and n is an integer of 1 to 4,

(Wherein R ³ is any one or more selected from the group consisting of C ₁ -C ₈ alkyl groups and hydrogen, and p is an integer of 1 to 5)

(Wherein R ⁴ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group, a phenyl group, a dimethylamine group and hydrogen, and q is an integer of 1 to 5), X Is iodine, bromine or chlorine.)

)은 요오드, 브롬 또는 염소를 포함하는 화합물이면 특별히 한정되는 것이 아니다.The halide compound (

) Is not particularly limited as long as it is a compound containing iodine, bromine or chlorine.

The amount of the halide compound to be used in the above production method is preferably 1.0 to 1.5 equivalents, more preferably 1.0 to 1.2 equivalents, based on the potassium ethynyl trifluoroborate derivative. The amount of the halide compound to be used is determined in consideration of the reaction efficiency with potassium ethynyltrifluoroborate. When the alkene compound is less than 1.0 equivalent, un-reacted potassium ethinyltrifluoroborate may remain, and when the equivalent amount is more than 1.5 equivalents, the halide compound is excessively left to deteriorate the economical efficiency and the yield and purity of the resulting product are lowered.

In the present invention, the catalyst may be a copper halide catalyst.

The copper halide catalyst is not particularly limited as long as it is a compound containing copper (Cu, Cooper), but is preferably copper iodide (CuI), copper bromide (CuBr), copper copper bromide dimethyl sulfide complex (CuBr.DMS) Oxide (Cu ₂ O), copper sulfate (CuSO ₄ ), and the like.

The amount of the catalyst to be used is preferably 0.01 to 0.2 equivalents, more preferably 0.03 to 0.1 equivalents, based on potassium ethinyl trifluoroborate. The amount of the catalyst to be used is in consideration of the reaction efficiency with potassium ethynyltrifluoroborate. When the amount of the catalyst is less than 0.01 equivalent, the reaction time is long and the unreacted potassium ethenyltrifluoroborate may remain in the resultant product. When the amount of the catalyst is more than 0.2 equivalent, the reaction proceeds rapidly, but the economical efficiency is lowered due to excessive use of expensive catalyst .

) 및 N,N’-디메틸시클로헥산-1,2-디아민(

) 중 하나 이상인 것일 수 있다. 상기 리간드의 사용량은, 사용되는 포타슘 에티닐트리플루오로보레이트에 대하여, 0.01내지 0.5당량인 것이 바람직하고, 더욱 바람직하게는 0.1내지 0.2당량일 수 있다. 상기 리간드의 사용량 범위는 촉매의 종류와 반응 효율을 고려한 것이다. 리간드의 사용량이 0.01 미만인 경우에는 촉매의 활성을 충분히 도울 수 없어 반응시간이 길어지고 수율이 저하되며, 0.5당량을 초과 시에는 반응은 빨리 진행되나 리간드의 과다 사용으로 인한 최종 결과물의 순도와 경제성이 저하된다.
The ligand used in the above production method is not particularly limited, but is preferably N , N' -dimethylethylenediamine (

) And N , N' -dimethylcyclohexane-1,2-diamine (

). ≪ / RTI > The amount of the ligand to be used is preferably 0.01 to 0.5 equivalents, more preferably 0.1 to 0.2 equivalents based on the amount of potassium ethinyl trifluoroborate to be used. The range of the amount of the ligand is based on the kind of the catalyst and the reaction efficiency. When the amount of the ligand is less than 0.01, the reaction can not be sufficiently assisted to increase the reaction time and the yield is lowered. When the amount exceeds 0.5 equivalent, the reaction proceeds rapidly, but the purity and economical efficiency of the final product due to excessive use of the ligand .

The inorganic salt to be used in the above production method is not particularly limited as a base, but it is preferably a salt of potassium carbonate (K ₂ CO ₃ ), sodium carbonate (Na ₂ CO ₃ ) and cesium carbonate (Cs ₂ CO ₃ ) Lt; / RTI > The amount of the inorganic salt to be used is preferably 0.1 to 2.0 equivalents, more preferably 1.0 to 1.2 equivalents, based on the potassium ethynyltrifluoroborate. When the amount of the inorganic salt is less than 1.0 equivalent, the reaction termination time becomes longer and the yield decreases. When the amount of the inorganic salt is more than 2.0 equivalents, the relative amount of the solvent increases and the starting material becomes unstable due to the strong base condition.

In the present invention, the additive may be sodium ascorbate as a reaction rate improver. The additive used in the above production method is used for the purpose of improving the reaction rate. The amount of the additive to be used is preferably 0.01 to 0.5 equivalents, more preferably 0.1 to 0.5 equivalents, based on the potassium ethynyl trifluoroborate. 0.2 equivalents. The amount of the additive to be used is in consideration of the reaction efficiency of potassium ethynyltrifluoroborate. When the amount of the additive to be used is less than 0.01, the potassium ethynyltrifluoroborate is not completely reacted and is mixed with the final product to lower the purity and yield. When the amount exceeds 0.5 equivalent, the purity of the final product due to excessive use of the additive .

The solvent used in the above production method is not particularly limited but is preferably a solvent such as N, N -dimethylformamide (DMF), dimethylsulfoxide (DMSO), methanol (MeOH), distilled water (H ₂ O) Or a mixed solvent of N, N -dimethylformamide and methanol or distilled water, a mixed solvent of dimethyl sulfoxide and methanol or distilled water, and a mixed solvent of N, N-dimethylformamide and dimethyl sulfoxide .

The reaction temperature of the above production method may vary depending on the reactants, but it is preferably 20 ° C to 150 ° C, more preferably 25 ° C to 60 ° C. If the reaction temperature is lower than 20 ° C, the reaction rate is significantly lowered and the reaction time may be prolonged. If the temperature rises to 150 ° C or more, the byproducts or the final product may be deformed, thereby lowering the purity and yield.

The reaction time of the process may vary depending on the reaction temperature and the amount of the reactant, but is preferably 10 minutes to 48 hours, more preferably 30 minutes to 12 hours.

The potassium organo- 1H -1,2,3-triazol-4-yl trifluorofluoroborate derivative prepared according to the above-described preparation method can be used as a starting material for the production of an organo-1,2,3-triazole derivative It is useful as a material. That is, the present invention includes a step of carrying out a carbon-carbon bonding reaction, a substitution reaction or an addition reaction using the above potassium organo- 1H -1,2,3-triazol-4-yl trifluoro borate derivative as a starting material Triazole derivative of formula < RTI ID = 0.0 > (I) < / RTI >

The carbon-carbon bond reaction is preferably carried out under a palladium catalyst, but is not limited thereto. For example, in a Suzuki-Miyaura carbon-carbon coupling reaction, which is a natural-friendly and stable carbon-carbon bonding reaction using a palladium catalyst, the potassium organo-1 H -1 , 2,3-triazol-4-yl trifluoroborate derivatives may serve as coupling reagents.

The substitution reaction or the addition reaction is preferably carried out under rhodium (Rh) catalyst, but is not limited thereto. For example, an addition reaction or a halogen substitution reaction using a rhodium (Rh) catalyst can be carried out.

The preparation method according to the present invention is characterized in that an organo-1,2,3-triazole obtained through a reaction between a known alkyne compound and an azide compound is expensive and requires various alkane compounds , It is characterized in that a novel organo 1,2,3-triazole compound can be produced more diversely and economically by replacing the alkane compound with potassium ethynyl trifluoroborate. Thus, the present inventors have succeeded in various organic synthesis reactions and production of optical organic materials, medicines, and all the synthesis of physiologically active natural products by the potassium organo-1 H -1,2,3-triazol-4-yl trifluoro borate derivatives It has an advantage that it can be utilized as a reactant widely used for the introduction reaction of the desired organo-1,2,3-triazole.

In addition, since the above-described production method according to the present invention is a single reaction, the manufacturing process is very fast, convenient, efficient and economical. In addition, since potassium organotrifluoroborate is stable to air and moisture as compared with organoboronic acid or organoboronate ester, it can be quantitatively reacted in a solid form which is easy to handle, so that it is more effective. Also in the production method, it is advantageous to easily prepare by adding potassium hydrogen fluoride (KHF ₂ ), which is relatively inexpensive to the organoboronic acid or organic boron ester. In terms of reactivity, the carbon-carbon bond reaction can be utilized in various ways because it is almost similar to the conventional organoboronic acid or organic boron ester.

The present invention will be described in more detail through the following examples. However, the examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

[Example 1] Synthesis of potassium 1-benzyl- 1H -1,2,3-triazol-4-yl trifluoroborate

N , N' -dimethylethylenediamine (8.8 mg, 20 mol) was added dropwise to a solution of the title compound (102.6 mg, 0.6 mmol), sodium azide (48.7 mg, 0.75 mmol), CuI 9.6 mg (10 mol%), cesium carbonate 9.9 mg (20 mol%) of sodium ascorbate and 66.0 mg (0.5 mmol) of potassium ethynyltrifluoroborate were dissolved in 3 ml of dimethylsulfoxide (DMSO) and 1 ml of distilled water (H ₂ O) , And reacted at 40 ^° C. After 0.5 hour of reaction, the insoluble salts were removed using celite and activated carbon. The filtered acetone solvent was concentrated and 5 mL of diethyl ether was added to the residue to obtain crystals. The resulting crystals were filtered and dried to give 119 mg (yield = 93%) of the title compound.

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.47 (s, 1H), 7.32 (m, 5H), 5.53 (s, 2H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 138.1, 129.5, 128.7, 128.6, 53.2.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -138.9.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.16.

FT-IR (ATR): 3148, 2084, 1640, 1519, 1456, 1203, 1131, 981, 924, 817, 716 cm ^-1 .

ESI-MS: m / z calcd for C 9 H 8 BF 3 N 3 [MK +] - 226.07, found 226.1.

Example 2 Potassium 1 - (3-phenylpropyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

Except that the starting material was replaced with 119 mg (0.6 mmol) of 3-bromopropylbenzene, the reaction mixture was purified after 0.5 hour reaction in the same manner as in Example 1, to obtain 117 mg (yield = 80%) of the title compound. .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.97 (s, 1H), 7.23 (m, 5H), 4.34 (t, 2H, J = 14.0 Hz), 2.61 (t, 2H, J = 15.6 Hz) , ≪ / RTI > 2.22 (m, 2H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 142.1, 129.3, 129.2, 126.8, 33.4, 32.8.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -140.7.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 3.16.

FT-IR (ATR): 3026, 2945, 2360, 1736, 1602, 1453, 946, 796, 748, 699 cm ^-1 .

ESI-MS: m / z calcd for C 11 H 12 BF 3 N 3 [MK +] - 254.11, found 254.1.

Example 3 Potassium 1- (4-methoxybenzyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted in the same manner as in Example 1, except that the starting material was replaced by 120 mg (0.6 mmol) of 4-methoxybenzyl bromide, and the reaction was conducted for 0.5 hour, followed by purification to obtain the title compound 137 mg (Yield = 93% .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.71 (s, 1H), 7.33 (d, 2H, J = 8.4 Hz), 7.00 (d, 2H, J = 8.8 Hz), 5.52 (s, 2H) , ≪ / RTI > 3.87 (s, 3H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 159.2, 129.1, 113.7, 54.6.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -140.7.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.34.

FT-IR (ATR): 3103, 2940, 2843, 2363, 2085, 1610, 1516, 1457, 1245, 1024, 948 cm ^-1 .

ESI-MS: m / z calcd for C 10 H 10 BF 3 N 3 O [MK ⁺ ] ^- 256.09, found 256.1.

Example 4 Potassium 1- (4-methylbenzyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted in the same manner as in Example 1, except that the starting material was replaced with 110 mg (0.6 mmol) of 4-methylbenzyl bromide, and the reaction was conducted for 0.5 hours, followed by purification to obtain 117 mg of the title compound (yield = 84%).

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.47 (s, 1H), 7.32 (m, 5H), 5.53 (s, 2H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 138.1, 129.5, 128.7, 128.6, 53.2.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -138.9.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.16.

FT-IR (ATR): 3148, 2084, 1640, 1519, 1456, 1203, 1131, 981, 924, 817, 716 cm ^-1 .

ESI-MS: m / z calcd for C 9 H 8 BF 3 N 3 [MK +] - 226.07, found 226.1.

Example 5 Potassium 1- (4-cyanobenzyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted in the same manner as in Example 1, except that the starting material was replaced by 118 mg (0.6 mmol) of 4-cyanobenzyl bromide, and the reaction was carried out for 0.5 hour, followed by purification to obtain 126 mg of the title compound (yield = 87%) .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.77 (d, 2H, J = 8.4 Hz), 7.61 (s, 1H), 7.47 (d, 2H, J = 8.0 Hz), 5.70 (s, 2H) .

¹³ C NMR (100 MHz, Acetone- d ₆ )? 143.4, 133.3, 129.5, 119.1, 112.5, 52.7.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -141.1.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.36.

FT-IR (ATR): 3117, 3039, 2229, 1610, 1418, 1258, 1218, 1119, 1000, 863 cm ^-1 .

ESI-MS: m / z calcd for C 10 H 7 BF 3 N 4 [MK +] - 251.07, found 251.1.

Example 6 Potassium 1- (3,5-difluorobenzyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

(Yield: 78%) was obtained in the same manner as in Example 1, except that the starting material was replaced by 124 mg (0.6 mmol) of 3,5-difluorobenzyl bromide. ).

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.60 (s, 1H), 6.93 (m, 3H), 5.65 (s, 2H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 165.1, 162.7, 142.5, 111.6, 103.8, 52.2.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -110.9, -140.1.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.86.

FT-IR (ATR): 3088, 2959, 1624, 1596, 1452, 1317, 1257, 998, 930 cm ^-1 .

ESI-MS: m / z calcd for C 9 H 6 BF 5 N 3 ^{[MK +] - 262.06, found} 262.0.

Example 7 Potassium 1- (2,6-difluorobenzyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

(Yield: 76%) of the title compound in the same manner as in Example 1, except that the starting material was replaced by 124 mg (0.6 mmol) of 2,6-difluorobenzyl bromide, ).

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.49 (m, 2H), 7.10 (d, 1H, J = 8.0 Hz), 7.08 (d, 1H, J = 8.0 Hz), 5.63 (s, 2H) .

¹³ C NMR (100 MHz, Acetone- d ₆ )? 200.5, 144.3, 133.2, 132.3, 127.3, 134.6, 34.0, 8.6.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -116.1, -141.6.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.13.

FT-IR (ATR): 2981, 2943, 1659, 1683, 1608, 1357, 1203, 1125, 952, 819 cm ^-1 .

ESI-MS: m / z calcd for C 9 H 6 BF 5 N 3 ^{[MK +] - 262.06, found} 262.0.

[Example 8] Synthesis of potassium 1-ethoxycarbonylmethyl- 1H -1,2,3-triazol-4-yl trifluoroborate

The reaction product was purified by the same method as in Example 1, except that the starting material was replaced by 100 mg (0.6 mmol) of ethyl 2-bromoacetate, to obtain 108 mg (Yield = 83%) of the title compound .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.70 (s, 1H), 5.26 (s, 2H), 4.20 (q, 2H, J = 6.8 Hz), 1.25 (t, 3H, J = 7.2 Hz) .

^{13 C NMR (100 MHz, Acetone-} d 6) δ 168.3, 62.1, 14.4.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -139.2.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.53.

FT-IR (ATR): 3107, 2992, 2360, 2127, 1748, 1624, 1597, 1452, 1214, 1119, 997 cm ^-1 .

ESI-MS: m / z calcd for C ₆ H ₈ BF ₃ N ₃ O ₂ [MK ^< ^{+ &} gt ^; ] ^- 222.07, found 222.1.

[Example 9] Synthesis of potassium 1-benzyloxycarbonylmethyl- 1H -1,2,3-triazol-4-yl trifluoroborate

The reaction was conducted for 0.5 hour and purified by the same method as in Example 1, except that 137 mg (0.6 mmol) of benzyl 2-bromoacetate was used as starting material, and 139 mg (yield = 86%) of the title compound was obtained.

¹ H NMR (400 MHz, Acetone- d ₆ )? 7.62 (s, 1H), 7.38 (m, 5H), 5.33 (s, 2H), 5.22 (s, 2H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 168.3, 136.7, 129.4, 129.1, 129.0, 67.7, 50.7.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -140.9.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.34.

FT-IR (ATR): 3134, 2948, 2110, 1746, 1621, 1388, 1211, 1143, 926 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 11 H 10 BF 3 N 3 O ₂ [M ^{+ &} gt ^; ] ^- 284.08, found 284.1.

Example 10 Potassium 1- (3-methoxycarbonyl benzyl) Synthesis of borate to -1 H -1,2,3- triazol-4-yl trifluoroacetate

(Yield: 78%) was obtained in the same manner as in Example 1, except that 137 mg (0.6 mmol) of methyl 3- (bromomethyl) benzoate was used as the starting material. ).

^{1 H NMR (400 MHz, Acetone-} d 6) δ 8.04 (d, 1H, J = 8.4 Hz), 7.97 (s, 1H), 7.69 (m, 3H), 5.66 (s, 2H), 3.97 (s, 3H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 166.0, 137.3, 132.0, 130.4, 128.8, 128.5, 128.1, 51.8, 51.5.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -138.7.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.22.

FT-IR (ATR): 3117, 2954, 1722, 1521, 1434, 1282, 1203, 1103, 1044, 948 cm ^-1 .

ESI-MS: m / z calcd for C 11 H 10 BF 3 N 3 O [MK +] - 284.08, found 284.1.

[Example 11] Synthesis of potassium 1,1 '- (1,4-phenylenebis (methylene)) bis (1 H -1,2,3-triazole) -4,4'-yl trifluoroborate

The same procedure as in Example 1 was repeated except that the starting material was replaced with 157 mg (0.6 mmol) of 1,4-bis (bromomethyl) benzene and 132.0 mg (1.0 mmol) of potassium ethynyltrifluoroborate For 0.5 hours, and then purified to obtain 150 mg of the title compound (yield = 80%).

¹ H NMR (400 MHz, DMSO- d ₆ )? 7.46 (s, 2H), 7.21 (s, 4H), 5.45 (s, 4H).

¹³ C NMR (100 MHz, DMSO- d ₆ )? 137.08, 128.4, 126.4, 51.9, 31.2.

^{19 F NMR (376 MHz, DMSO-} d 6) δ -135.5.

^{11 B NMR (128 MHz, DMSO-} d 6) δ 2.06.

FT-IR (ATR): 2954, 2040, 1721, 1522, 1435, 1127, 931 cm ^-1 .

ESI-MS: m / z calcd for C 12 H 10 B 2 F 6 N 6 ^{[MK +] - 374.11, found} .

Example 12 Potassium 1- (4-bromobenzyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted for 0.5 hour and purified by the same method as in Example 1, except that 149 mg (0.6 mmol) of 4-bromobenzyl bromide was used as starting material, to obtain 146 mg of the title compound (yield = 85%).

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.54 (d, 2H, J = 8.0 Hz), 7.50 (s, 1H), 7.20 (d, 2H, J = 8.0 Hz), 5.47 (s, 1H) .

^{13 C NMR (100 MHz, Acetone-} d 6) δ 136.5, 131.4, 129.9, 126.0, 120.8, 50.9.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -137.3.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.06.

FT-IR (ATR): 3138, 3101, 2061, 1489, 1127, 926 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 9 H 7 BBrF 3 N 3 ^{[MK +] - 303.99, found} 304.0, 306.0.

Example 13 Potassium 1- (4-trifluoromethylbenzyl) -1 H -1,2,3- triazol-4-yl Synthesis of borate trifluoroacetate

135 mg (Yield = 81%) of the title compound was obtained by the same procedure as in Example 1, except that 144 mg (0.6 mmol) of 4-trifluoromethylbenzyl bromide was used as the starting material. .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.71 (d, 2H, J = 8.0 Hz), 7.63 (s, 1H), 7.50 (d, 2H, J = 8.0 Hz), 5.69 (s, 2H) .

^{13 C NMR (100 MHz, Acetone-} d 6) δ 167.5, 146.9, 133.1, 132.1, 127.2, 116.3, 60.5, 14.7.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -63.1, 140.5.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.56.

FT-IR (ATR): 3344, 2977, 1694, 1628, 1362, 1321, 1305, 1210, 1175, 1039, 944, 814, 722, 631 cm ^-1 .

ESI-MS: m / z calcd for C 10 H 7 BF 6 N 3 [MK +] - 294.06, found 294.1.

Example 14 Potassium 1- (methyl-benzyl-3-trifluoromethyl) -1 H -1,2,3- triazol-4-yl Synthesis of the borate with trifluoroacetic

135 mg (Yield = 81%) of the title compound was obtained by the same procedure as in Example 1, except that 144 mg (0.6 mmol) of 4-trifluoromethylbenzyl bromide was used as the starting material. .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.64 (m, 5H), 5.67 (s, 2H).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 167.1, 143.9, 133.2, 133.0, 126.9, 116.3, 37.3, 35.6.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -63.1, -138.6.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.68.

FT-IR (ATR): 3373, 1644, 1584, 1492, 1397, 1368, 1334, 1156, 1083, 1042, 1011, 960, 814, 735, 627 cm ^-1 .

ESI-MS: m / z calcd for C 10 H 7 BF 6 N 3 [MK +] - 294.06, found 294.1.

Example 15 Potassium 1- (4-nitrobenzyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted for 0.5 hour and purified by the same method as in Example 1, except that 129 mg (0.6 mmol) of 4-nitrobenzyl bromide was used as starting material, to obtain 126 mg (yield = 81%) of the title compound.

^{1 H NMR (400 MHz, Acetone-} d 6) δ 8.20 (d, 2H, J = 8.8 Hz), 7.66 (s, 1H), 7.52 (d, 1H, J = 8.4 Hz), 5.75 (s, 2H)

^{13 C NMR (100 MHz, Acetone-} d 6) δ 148.5, 145.4, 129.7, 127.0, 124.6, 52.5.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -139.6.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.49.

FT-IR (ATR): 3015, 2955, 1672, 1615, 1438, 1346, 1280, 1204, 1178, 947, 931 cm ^-1 .

ESI-MS: m / z calcd for C 9 H 7 BF 3 N 3 O 2 [MK +] - 271.06, found 271.1.

[Example 16] Synthesis of potassium 1-allyl- 1H -1,2,3-triazol-4-yl trifluoroborate

80 mg (yield = 74%) of the title compound was obtained by following the same procedure as in Example 1, except that the starting material was replaced with allyl bromide (72 mg, 0.6 mmol).

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.56 (s, 1H), 6.06 (m, 1H), 5.21 (d, 1H, J = 8.4 Hz), 5.19 (d, 1H, J = 14.0 Hz) , 4.96 (d, 2H, J = 6.0 Hz).

¹³ C NMR (100 MHz, Acetone- d ₆ )? 134.3, 118.4, 52.3.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -139.6.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.43.

FT-IR (ATR): 3134, 2046, 1645, 1519, 1417, 1143, 991, 927 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 5 H 6 BF 3 N 3 [MK ⁺ ] ^- 176.06, found 176.1.

[Example 17] Synthesis of potassium 1-phenyl- 1H -1,2,3-triazol-4-yl trifluoroborate

A. A mixture of 122 mg (0.6 mmol) of iodobenzene, 48.7 mg (0.75 mmol) of sodium azide, 9.6 mg (10 mol%) of CuI, 8.8 mg (20 mol%) of N , N' -dimethylethylenediamine, 9.9 mg (20 mol%) of Na-ascorbate and 66.0 mg (0.5 mmol) of potassium ethynyltrifluoroborate were dissolved in a mixed solvent of 3 ml of dimethylsulfoxide (DMSO) and 1 ml of distilled water (H ₂ O) And reacted at 30 ^° C. After 0.5 hour of reaction, the insoluble salts were removed using celite and activated carbon. The filtered acetone solvent was concentrated and 5 mL of diethyl ether was added to the residue to obtain crystals. The resulting crystals were filtered and dried to obtain 107 mg (yield = 84%) of the title compound.

B. The reaction was conducted for 0.5 hour and purified by the same method as in Example 17A, except that 93 mg (0.6 mmol) of bromobenzene was used as starting material, to give 117 mg (yield = 93%) of the title compound.

^{1 H NMR (400 MHz, Acetone-} d 6) δ 8.05 (s, 1H), 7.87 (d, 2H, J = 8.0 Hz), 7.55 (q, 2H, J = 8.0 Hz), 7.41 (q, 1H, J = 7.6 Hz).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 130.5, 128.4, 120.8.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -139.9.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.21.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C ₈ H ₆ BF ₃ N ₃ [MK ⁺ ] ^- 212.06, found 212.1.

[Example 18], potassium 1- (4-methoxyphenyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

A. Preparation of 124 mg (Yield = 88%) of the title compound in the same manner as in Example 17A, except that the starting material was replaced by 140 mg (0.6 mmol) of 4-iodoanisole, .

B. The reaction was conducted for 0.5 hours and then purified by the same method as in Example 17A, except that 112 mg (0.6 mmol) of 4-bromoanisole was used in the starting material. 124 mg (Yield = 88%) of the title compound was obtained .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.96 (s, 1H), 7.75 (d, 2H, J = 8.8 Hz), 7.08 (q, 2H, J = 9.2 Hz), 3.86 (s, 1H) .

¹³ C NMR (100 MHz, Acetone- d ₆ )? 160.0, 122.4, 115.5, 56.0.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -141.8.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.04.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 9 H 8 BF 3 N 3 O [MK ⁺ ] ^- 242.07, found 242.0.

Example 19 Potassium 1- (3-methoxyphenyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted for 0.5 hour and purified by the same method as in Example 17A, except that the starting material was used in place of 140 mg (0.6 mmol) of 3-iodoanisole, to obtain 121 mg (yield = 86%) of the title compound .

¹ H NMR (400 MHz, Acetone- d ₆ )? 8.07 (s, 1H), 7.44 (s, 3H), 6.98 (s, 1H), 3.90 (s, 3H).

¹³ C NMR (100 MHz, Acetone- d ₆ )? 161.6, 139.9, 131.4, 124.3, 114.3, 112.9, 106.5, 55.9.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -141.9.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.33.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 9 H 8 BF 3 N 3 O [MK ⁺ ] ^- 242.07, found 242.0.

[Example 20], potassium 1- (2-methoxyphenyl) Synthesis of borate to -1 H -1,2,3- triazol-4-yl trifluoroacetate

The reaction was carried out for 0.5 hours and then purified by the same method as in Example 17A, except that the starting material was used in place of 140 mg (0.6 mmol) of 3-iodoanisole, and 124 mg (Yield = 88%) of the title compound was obtained .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.96 (s, 1H), 7.75 (d, 2H, J = 8.8 Hz), 7.08 (q, 2H, J = 9.2 Hz), 3.86 (s, 1H) .

¹³ C NMR (100 MHz, Acetone- d ₆ )? 160.0, 122.4, 115.5, 56.0.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -141.8.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.04.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 9 H 8 BF 3 N 3 O [MK ⁺ ] ^- 242.07, found 242.0.

Example 21 Potassium 1- (4-trifluoromethylphenyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

136 mg (Yield = 85%) of the title compound was obtained after the reaction for 0.5 hours and purification by the same method as in Example 17A, except that 163 mg (0.6 mmol) of 4-iodobenzotrifluoride was used as the starting material. .

^{1 H NMR (400 MHz, Acetone-} d 6) δ 8.21 (s, 1H), 8.17 (d, 2H, J = 8.4 Hz), 7.92 (d, 2H, J = 8.8 Hz.

^{13 C NMR (100 MHz, Acetone-} d 6) δ 152.5, 130.3, 126.3, 121.7, 113.6, 56.4.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -62.9, -141.2.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.71.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C ₈ H ₆ BF ₃ N ₃ [MK ⁺ ] ^- 212.06, found 212.1.

Example 22 Potassium 1- (3-trifluoromethylphenyl) -1 H -1,2,3- triazol-4-yl Synthesis of the borate with trifluoroacetic

(Yield: 89%) of the title compound in the same manner as in Example 17A, except that the starting material was used in place of 163 mg (0.6 mmol) of 3-iodobenzotrifluoride. .

¹ H NMR (400 MHz, Acetone- d ₆ )? 8.25 (m, 2H), 8.22 (d, 1H, J = 8.8 Hz), 7.82 (t, 1H, J = 15.6 Hz).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 152.5, 130.3, 126.3, 121.7, 113.6, 56.4.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -6339, -141.3.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.78.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C ₈ H ₆ BF ₃ N ₃ [MK ⁺ ] ^- 212.06, found 212.1.

[Example 23], potassium 1- (4-aminophenyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted for 0.5 hour and purified by the same method as in Example 17A, except that 131 mg (0.6 mmol) of 4-iodoaniline was used as starting material, to obtain 125 mg (yield = 94%) of the title compound.

^{1 H NMR (400 MHz, Acetone-} d 6) δ 7.95 (s, 1H), 7.49 (d, 2H, J = 8.4 Hz), 7.78 (s, 2H, J = 8.4 Hz), 5.06 (s, 2H) .

^{13 C NMR (100 MHz, Acetone-} d 6) δ 152.5, 130.3, 126.3, 121.7, 113.6, 56.4.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -6339, -141.3.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.78.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 8 H 7 BF 3 N 4 [MK ⁺ ] ^- 227.07, found 212.1.

[Example 24], potassium 1- (4-hydroxyphenyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The reaction was conducted for 0.5 hour and purified by the same method as in Example 17A, except that 132 mg (0.6 mmol) of 4-iodophenol was used as the starting material, and 113 mg (Yield = 85%) of the title compound was obtained.

^{1 H NMR (400 MHz, Acetone-} d 6) δ 9.46 (s, 1H), 7.93 (s, 1H), 7.64 (d, 2H, J = 9.2 Hz), 7.10 (d, J = 8.8 Hz).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 158.2, 131.2, 124.5, 122.7, 116.9.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -141.3.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.16.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 8 H 6 BF 3 N 4 O [MK ⁺ ] ^- 228.06, found 212.1.

[Example 25], potassium 1- (3-hydroxyphenyl) -1 H-1,2,3-triazole in the synthesis of borate-4-yl trifluoroacetate

The title compound was obtained in 115 mg (Yield = 86%) by the same method as in Example 17A, except that the starting material was replaced by 132 mg (0.6 mmol) of 3-iodophenol.

^{1 H NMR (400 MHz, Acetone-} d 6) δ 9.71 (s, 1H), 7.99 (s, 1H), 7.40 (s, 1H), 7.31 (m, 2H), 6.86 (d, 1H, J = 11.2 Hz).

^{13 C NMR (100 MHz, Acetone-} d 6) δ 152.5, 130.3, 126.3, 121.7, 113.6, 56.4.

^{19 F NMR (376 MHz, Acetone-} d 6) δ -6339, -141.3.

^{11 B NMR (128 MHz, Acetone-} d 6) δ 2.78.

FT-IR (ATR): 3134, 3060, 2130, 2013, 1602, 1522, 1211, 970 cm < ^{-1 &} gt ;.

ESI-MS: m / z calcd for C 8 H 7 BF 3 N 4 [MK ⁺ ] ^- 228.06, found 212.1.

Claims (20)

1. A potassium organo- 1H -1,2,3-triazol-4-yl trifluoroperate derivative represented by the following formula (1).
[Chemical Formula 1]

(In Formula 1,
R ¹ represents a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ alkyl ether group,

Group (Ar represents at least one selected from the group consisting of phenyl, biphenyl, naphthyl, phenoxy, phenyl, pyridyl, furanyl and thiophenyl, R ² is C ₁ -C ₈ alkyl, C ₁ -C ₄ A C ₁ -C ₄ alkylthio group, a C ₆ -C ₁₂ aryloxy group, a C ₁ -C ₄ alkyl group substituted with at least one halogen, a C ₁ -C ₄ alkyloxy group substituted with at least one halogen , Nitro group (-NO ₂ ), cyano group (-CN), fluorine, chlorine, bromine, iodine, and hydrogen, m is an integer of 0 to 5, 4 < / RTI >

(Wherein R ³ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group and hydrogen, p is an integer of 1 to 5), and

(Wherein R ⁴ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group, a phenyl group, a dimethylamine group and hydrogen, and q is an integer of 1 to 5). The method of claim 1,
The potassium organo-1 H -1,2,3-triazol-4-yl trifluoro borate derivative is obtained by reacting potassium 1-benzyl- 1H -1,2,3-triazol-4-yl trifluoro borate, potassium 1- (3-phenylpropyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (4-methoxybenzyl) -1 H -1,2, 3-triazol-4-yl-trifluoromethyl borate, potassium 1- (4-methylbenzyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (4-cyano Benzyl) -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (3,5-difluorobenzyl) -1 H -1,2,3-triazole- 4-yl trifluoroborate, potassium 1- (2,6-difluorobenzyl) -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1-ethoxycarbonylmethyl -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1-benzyloxycarbonylmethyl-1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (3-methoxycarbonyl-benzyl) -1 H -1,2 , 1,1 '- (1,4-phenylenebis (methylene)) bis ( 1H -1,2,3-triazole) -4,4 '-yl trifluoromethyl borate, potassium 1- (4-bromobenzyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (4-trifluoromethyl-benzyl ) -1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (3-trifluoromethylbenzyl) -1 H -1,2,3-triazol- trifluoroacetic borate, potassium 1- (4-nitrobenzyl) -1 H -1,2,3- triazol-4-yl-trifluoro-borate, potassium l-allyl -1 H -1,2,3- triazol 1-phenyl-1 H -1,2,3-triazol-4-yl trifluoroborate, potassium 1- (4-methoxyphenyl) -1 H -1 , 2,3-triazol-4-yl-trifluoro-borate, potassium 1- (3-methoxyphenyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (2-methoxyphenyl) -1 H -1,2,3- triazol-4-yl trifluoroacetate Rate, a potassium 1- (4-trifluoromethylphenyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- (3-trifluoromethylphenyl) -1 H -1 , 2,3-triazol-4-yl-trifluoro-borate, potassium 1- (4-aminophenyl) -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate, potassium 1- ( 4-hydroxyphenyl) -1 H -1,2,3-triazol-4-yl trifluoroborate, and potassium 1- (3-hydroxyphenyl) -1 H -1,2,3-triazole It is one selected from the group consisting of borate-4-yl-trifluoromethyl potassium organo -1 H -1,2,3- triazol-4-yl-trifluoromethyl borate derivative. A process for the preparation of potassium organo- 1H -1,2,3-triazol-4-yl trifluoroacetate according to claim 1, comprising reacting potassium ethynyltrifluoroborate, sodium azide and halide compounds under catalysis Lt; / RTI > The method of claim 3, wherein
A method for producing a potassium organo -1 H -1,2,3- triazol-4-yl tree borate derivative fluoro that the manufacturing method is represented by scheme 1 below.
[Reaction Scheme 1]

(In the above Reaction Scheme 1,
R ¹ represents a C ₁ -C ₈ alkyl group, a C ₆ -C ₁₂ cycloalkyl group, a C ₆ -C ₁₅ arylalkyl group, a C ₂ -C ₉ alkyl ether group,

Group (Ar represents at least one selected from the group consisting of phenyl, biphenyl, naphthyl, phenoxy, phenyl, pyridyl, furanyl and thiophenyl, R ² is C ₁ -C ₈ alkyl, C ₁ -C ₄ A C ₁ -C ₄ alkylthio group, a C ₆ -C ₁₂ aryloxy group, a C ₁ -C ₄ alkyl group substituted with at least one halogen, a C ₁ -C ₄ alkyloxy group substituted with at least one halogen , Nitro group (-NO ₂ ), cyano group (-CN), fluorine, chlorine, bromine, iodine, and hydrogen, m is an integer of 0 to 5, 4 < / RTI >

(Wherein R ³ is any one or more selected from the group consisting of C ₁ -C ₈ alkyl groups and hydrogen, and p is an integer of 1 to 5)

(Wherein R ⁴ is any one or more selected from the group consisting of a C ₁ -C ₈ alkyl group, a phenyl group, a dimethylamine group and hydrogen, and q is an integer of 1 to 5)
X is a halogen element.) The method of claim 3, wherein
The preparation method comprises reacting at least one member selected from the group consisting of a ligand, an additive and an inorganic salt together, wherein the potassium organo- 1H -1,2,3-triazol-4-yl trifluoro borate derivative Way. The method of claim 3, wherein
Wherein the catalyst is a copper halide catalyst, wherein the catalyst is a copper organo- 1H -1,2,3-triazol-4-yl trifluoroborate derivative. The method according to claim 6,
The keopeo halide catalysts are selected from the group consisting of keopeo iodide (CuI), keopeo bromide (CuBr), keopeo bromide dimethylsulfide complex (CuBr · DMS), keopeo oxide (Cu ₂ O), keopeo sulfate (CuSO ₄₎ Lt; RTI ID = 0.0 > 1- H -1, < / RTI > 2,3-triazol-4-yl trifluorofluoroborate derivative. The method of claim 3, wherein
The catalyst is potassium borate and 0.01 to 0.2 equivalents relative to trifluoroacetic ethynyl potassium organo -1 H -1,2,3- method for producing a borate derivative as triazol-4-yl trifluoroacetate. The method of claim 3, wherein
Wherein said halide compound is 1.0 to 1.5 equivalents of potassium ethynyl trifluoroborate derivative. 2. A process for producing a potassium organo- 1H -1,2,3-triazol-4-yl trifluoroborate derivative according to claim 1, 6. The method of claim 5,
Wherein the ligand is at least one of N , N' -dimethylethylenediamine and N , N' -dimethylcyclohexane-1,2-diamine, wherein the ligand is selected from the group consisting of potassium organo-1 H -1,2,3-triazol- Lt; / RTI > 6. The method of claim 5,
Wherein the ligand is 0.01 to 0.5 equivalents of potassium ethynyl trifluoroborate. 2. A process for preparing a potassium organo- 1H -1,2,3-triazol-4-yl trifluoroborate derivative according to claim 1, 6. The method of claim 5,
Wherein the additive is sodium ascorbate. ≪ RTI ID = 0.0 > 11. < / RTI > 6. The method of claim 5,
Wherein the additive is 0.01 to 0.5 equivalents of potassium ethynyl trifluoroborate. 2. A process for preparing a potassium organo- 1H -1,2,3-triazol-4-yl trifluoroborate derivative according to claim 1, 6. The method of claim 5,
The inorganic salt is potassium carbonate (K ₂ CO _3), sodium carbonate (Na ₂ CO ₃₎ and cesium carbonate (Cs ₂ CO _3), potassium organo at least one selected from the group consisting of: -1 H -1,2,3- Lt; / RTI > trifluoro borate derivative. 6. The method of claim 5,
Wherein the inorganic salt is 0.1 to 2.0 equivalents of potassium ethynyl trifluoroborate. 2. The process for producing a potassium organo- 1H -1,2,3-triazol-4-yl trifluoro borate derivative according to claim 1, The method of claim 3, wherein
The reaction is N, N - dimethylformamide (DMF), dimethyl sulfoxide (DMSO), methanol (MeOH), the potassium organo -1 H being formed in at least one solvent selected from the group consisting of water or a mixed solvent -1,2,3-triazol-4-yl trifluorofluoroborate derivative. The method of claim 3, wherein
The manufacturing method A method for producing a potassium organo -1 H -1,2,3- triazol-4-yl tree borate derivative fluorophenyl will be performed at temperature between 20 ℃ to 150 ℃ 10 minutes to 48 hours. A carbon-carbon bond reaction, a substitution reaction or an addition reaction using the potassium organo-1 H -1,2,3-triazol-4-yltrifluoroborate derivative according to claim 1 as a starting material Method for preparing organo 1,2,3-triazole derivatives. 19. The method of claim 18,
The carbon-carbon bonding reaction is carried out under a palladium catalyst. 19. The method of claim 18,
Wherein the substitution reaction or the addition reaction proceeds under a rhodium catalyst.