CN114181090A - Preparation method for synthesizing amine compound by amide through iridium and boron reagent co-catalysis hydrosilation - Google Patents

Preparation method for synthesizing amine compound by amide through iridium and boron reagent co-catalysis hydrosilation Download PDF

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CN114181090A
CN114181090A CN202010969949.8A CN202010969949A CN114181090A CN 114181090 A CN114181090 A CN 114181090A CN 202010969949 A CN202010969949 A CN 202010969949A CN 114181090 A CN114181090 A CN 114181090A
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amide
iridium
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黄培强
韩丰
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Xiamen University
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    • C07C209/50—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acid amides
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    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
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Abstract

The preparation method for synthesizing the amine compound by amide through the catalytic hydrosilylation of iridium and boron reagents comprises the following steps: in an organic solvent, amide and silane react under the catalysis of an iridium complex and a boron reagent, and then amine is obtained through concentration and purification; the molar ratio of the amide to the iridium complex to the boron reagent to the silane is 1: 0.0001-0.001: 0.01-0.05: 2-4; the invention takes stable and easily obtained amide as a raw material, uses iridium complex with very low catalyst loading capacity and a boron reagent to carry out co-catalytic hydrosilation, and efficiently synthesizes the amine compound. The method has the advantages of simple operation and separation of all steps, high reaction rate, mild reaction conditions, cheap and easily-obtained commercial reagents, high yield and good tolerance of functional groups.

Description

Preparation method for synthesizing amine compound by amide through iridium and boron reagent co-catalysis hydrosilation
Technical Field
The invention relates to the field of preparation of amine compounds, in particular to a preparation method for synthesizing amine compounds by amide through hydrosilylation catalyzed by iridium and boron reagents.
Background
Amines, as an important class of compounds, are often biologically active natural products and important building blocks in pharmaceutical molecules, such as the novel antidepressants Escitalopram (Escitalopram,2.1 and Clomipramine (Clomipramine,2.5), the atypical antipsychotics Aripiprazole (Aripiprazole 2.2 and the quinolone antibiofloxacin Levofloxacin (Levofloxacin,2.3), Fenspiride (Fenspiride,2.4) for the treatment of chronic bronchitis and respiratory insufficiency, and the calcium blockers for lowering blood pressure and preventing the angina drug Diltiazem (Ditiazem, 2.6).
Figure BDA0002682736360000011
Amine compounds have wide applications in the fields of medicines, pesticides, and the like, and at present, many methods have been developed for the preparation of amines. The conventional amine synthesis method refers to a general method for synthesizing amine compounds by heating (or high pressure) with a conventional heater in the presence of a catalyst, and several methods for synthesizing amines are described below.
The nitro compound is chemically reduced or catalytically hydrogenated to synthesize amine, and the chemical reduction is divided into metal reduction and metal hydride reduction.
Reductive amination is a simple method of converting an aldehyde ketone to an amine. Reductive amination of aldehydes and ketones can be carried out in two steps, first by dehydration of the carbonyl group with an amine to give the imine (Schiff base), which is then reduced to the amine by sodium borohydride or sodium cyanoborohydride.
The nitrile group is easily reduced to primary amine, the method for preparing primary amine by reducing the nitrile group by hydrogenation is mature in process, and a plurality of catalysts such as platinum oxide, nickel, palladium, cobalt, nickel boride and the like can be used for catalyzing the hydrogenation reduction of nitrile.
Reduction of the azide, which can be conveniently introduced into an organic molecule by an inorganic azide, is primarily a nucleophilic substitution of the halogen (usually bromine) in the molecule, which is then reduced to the amine by a suitable reagent. In addition, the amino group can be protected by reducing the azide group to the amino group with an appropriate reagent under mild conditions. The method can also be used for preparing amine compounds which are difficult to synthesize by other methods.
When amide without substituent on nitrogen atom reacts with alkali solution of sodium hypochlorite or sodium hypobromite, carbonyl is removed to generate primary amine, and carbon chain is reduced by one carbon atom in the reaction. This is a process found in hofmann for the production of amines and is commonly referred to as hofmann degradation.
Amide reduction is one of the important reactions in organic synthesis and is a common method for synthesizing amines. By selecting suitable reaction conditions, the amide (including lactam) can be reduced to different target products such as aldehyde, alcohol, imine or amine, wherein the reduction of amide to amine is most important. Conventional amide reduction to amines requires multiple steps. For example, first with Lawesson's reagent or P4S10The amide is made into thioamide, and then the amide is reduced into amine through two steps by using Ni reagent through desulfurization.
Figure BDA0002682736360000021
In the last decade, catalytic direct reduction methods of many metals such as Mo, Ru, Co, Rh, Ir, Os, Pt, In, Ti, Mn, etc. have been developed, but all of them have little practical application value because of the difficulty In obtaining catalysts or the harsh reaction conditions.
Disclosure of Invention
The invention aims to solve the problems in the prior art and provides a preparation method for synthesizing an amine compound by amide through hydrosilylation catalyzed by iridium and boron reagents, which takes stable and easily obtained amide as a raw material and synthesizes the amine compound with high yield through hydrosilylation catalyzed by an iridium complex and boron reagents.
In order to achieve the purpose, the invention adopts the following technical scheme:
the preparation method for synthesizing the amine compound by amide through the catalytic hydrosilylation of iridium and boron reagents comprises the following steps: in an organic solvent, amide and silane react under the catalysis of an iridium complex and a boron reagent, and then amine is obtained through concentration and purification; the synthetic route is as follows:
Figure BDA0002682736360000022
wherein R is1And R2Selected from hydrogen, alkyl or aryl; r3Selected from hydrogen, alkyl, aryl or alkoxy; [ Ir ]]Is an iridium complex, [ B ]]Is a boron reagent and Si-H is silane.
The alkyl is selected from C1-C20, the aryl is selected from C6-C20, and the alkoxy is selected from C1-C7.
In the invention, the molar ratio of the amide, the iridium complex, the boron reagent and the silane is 1: 0.0001-0.001: 0.01-0.05: 2-4.
The iridium complex comprises IrCl (CO) (PPh)3)2。
The boron reagent comprises (C)6F5)3B (tris-pentafluorophenyl boron).
The silane is selected from alkoxysilanes or alkylsilanes, e.g. (EtO)3SiH (triethoxysilane), Et3SiH (triethylsilane), PMHS (polymethylhydrosilane), TMDS (1,1,3, 3-tetramethyldisiloxane), Et2SiH2(diethylsilane) or Ph2SiH2(diphenylsilane) and the like.
The organic solvent is selected from ether, halogenated hydrocarbon or aromatic hydrocarbon. The ether is selected from C2-C6 ether, and the halogenated hydrocarbon is selected from C1-C6 halogenated hydrocarbon. Preferably, the organic solvent is selected from tetrahydrofuran, 2-methyltetrahydrofuran, dichloromethane, dichloroethane, toluene or xylene.
Compared with the prior art, the technical scheme of the invention has the following beneficial effects:
the invention takes stable and easily obtained amide as a raw material, uses iridium complex with very low catalyst loading capacity and a boron reagent to carry out co-catalytic hydrosilation, and efficiently synthesizes the amine compound. The method has the advantages of simple operation and separation of all steps, high reaction rate, mild reaction conditions, cheap and easily-obtained commercial reagents, high yield and good tolerance of functional groups.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present invention clearer and more obvious, the present invention is further described in detail below with reference to the following embodiments.
Example 1
Synthesis of N-methyl-N- (2-naphthyl) aniline (a)
Figure BDA0002682736360000031
N-methyl-N-phenyl-2-naphthamide (261mg) was dissolved in toluene, and iridium complex [ IrCl (CO) (PPh) was added in this order at room temperature3)2](8mg), silane TMDS (1,1,3, 3-tetramethyldisiloxane) (0.36mL) and B (C)6F5)3(15 mg). The reaction was stirred and concentrated to obtain a white solid a (240mg, 97% yield) after purification. IR (film) vmax:3052,2962,2819,1598,1505,1367,1119,939,812,747cm-1；1H NMR(400MHz,CDCl3)δ3.02(s,3H),4.63(s,2H),6.66-6.83(m,2H),7.17-7.28(m,2H),7.30-7.50(m,3H),7.60-7.69(m,1H),7.71-7.85(m,3H)ppm；13C NMR(100MHz,CDCl3)δ38.6,57.1,112.5,112.6,116.8,125.2,125.3,125.6,126.2,127.7,128.4,129.3,132.8,133.6,136.7,149.9ppm；MS(ESI,m/z):247(M+H+)。
Example 2
Synthesis of 1-benzyl azepane (b)
Figure BDA0002682736360000041
1-Benzylazan-2-one (203mg) was dissolved in tetrahydrofuran, and the iridium complex [ IrCl (CO) (PPh) was added in this order at room temperature3)2](8mg，1mol％)，B(C6F5)3(15mg) and silane TMDS (1,1,3, 3-tetramethyldisiloxane) (0.36 mL). After stirring the reaction was concentrated to give colorless liquid b (168mg, yield 89%)。IR(film)vmax:3021,2921,2847,2979,1490,1453,1353cm-1；1H NMR(400MHz,CDCl3)δ1.67(s,8H),2.68(s,4H),3.69(s,2H),7.21-7.49(m,5H)ppm；13C NMR(100MHz,CDCl3)δ27.0,28.2,55.6,62.7,126.6,128.0,128.7,140.0ppm；MS(ESI,m/z):189.4(M+H+)。
Example 3
Synthesis of naftifine (c)
Figure BDA0002682736360000042
N-methyl-N- (1-naphthylmethyl) cinnamamide (301mg) was dissolved in toluene, and iridium complex [ IrCl (CO) (PPh) was added in this order at room temperature3)2](8mg,1 mol%), TMDS (0.36mL) and B (C)6F5)3(15 mg). The reaction was stirred and concentrated to give a pale yellow liquid c after purification (178mg, yield 62%). IR (film) vmax:3022,2985,2782,1494,1369,1065cm-1；1H NMR(400MHz,CDCl3)δ2.27(s,3H),3.27(dd,J＝6.6,1.1Hz,2H),3.94(s,2H),6.36(dt,J＝15.9,6.6Hz,1H),6.56(d,J＝15.9Hz,1H),7.24-7.17(m,1H),7.33-7.27(m,2H),7.55-7.35(m,6H),7.76(d,J＝8.0Hz,1H),7.83(dd,J＝8.3,1.0Hz,1H),8.30(d,J＝8.4Hz,1H)ppm；13C NMR(100MHz,CDCl3)δ42.4,60.0,60.4,124.6,125.1,125.5,125.9,126.3,127.3,127.4,127.5,127.9,128.4,128.5,132.4,132.6,133.8,134.8,137.1ppm；MS(ESI,m/z):287.1(M+H+)。
Example 4
Synthesis of tribenzylamine (d)
Figure BDA0002682736360000051
N, N-dibenzylbenzamide (301mg) was dissolved in toluene, and the iridium complex [ IrCl (CO) (PPh) was added in this order at room temperature3)2](0.08mg,0.01 mol%), silanemeDS (0.36mL) and B (C)6F5)3(15 mg). Stirring for reaction, concentrating, and purifying to obtainLight yellow liquid d (281mg, 98% yield). IR (film) vmax:3082,3062,3028,2925,2881,2837,2802,1603,1493,1452,1366,1247,1122,1028cm-1；1H NMR(400MHz,CDCl3)δ3.55(s,6H),7.18-7.26(m,3H),7.26-7.35(m,6H),7.37-7.43(m,6H)ppm；13C NMR(100MHz,CDCl3)δ57.9,126.9,128.2,128.8,139.7ppm；MS(ESI,m/z):288.3(M+H+).
Example 5
Synthesis of N, N-dibenzylhexadecylamine (e)
Figure BDA0002682736360000052
N, N-dibenzylpalmitamide (435mg) was dissolved in toluene, and the iridium complex [ IrCl (CO) (PPh) was added thereto in this order at room temperature3)2](0.08mg,0.01 mol%), silanemeDS (0.36mL) and B (C)6F5)3(15 mg. after stirring the reaction, concentrated and purified to give a pale yellow liquid e (391mg, 93% yield.) IR (film) vmax:3085,3027,3026,2924,2793,1601,1453,1365,1259,1074,743,697cm-1；1H NMR(500MHz,CDCl3)δ0.87(t,J＝7.1Hz,3H),1.16-1.32(m,26H),1.45-1.53(m,2H),2.38(t,J＝7.2Hz,2H),3.53(s,4H),7.16-7.20(m,2H),7.26-7.29(m,4H),7.34-7.35(m,4H)ppm；13C NMR(125MHz,CDCl3)δ14.1,22.7,27.0,27.3,29.4,29.5,29.7(2C),29.70(2C),29.73(4C),31.95,53.42,58.3,126.7,128.1,128.7,140.1ppm；HRMS-ESI calcd for[C30H48N]+(M+H+):422.3781；found:422.3784.
Example 6
Synthesis of dibenzylamine (f)
Figure BDA0002682736360000053
N-Benzylbenzamide (211mg) was dissolved in toluene, and the iridium complex [ IrCl (CO) (PPh) was sequentially added thereto at room temperature3)2](8mg,1 mol%), silane TMDS (0.36mL) and B (C)6F5)3(30 mg). The reaction was stirred and concentrated to give a pale yellow liquid f (63mg, yield 32%) after purification. IR (film) vmax:3332,3083,3061,3024,2917,2817,1494,1452,1109,1027cm-1；1H NMR(400MHz,CDCl3)δ1.68(s,1H),3.80(s,4H),7.19-7.40(m,10H)ppm；13C NMR(100MHz,CDCl3)δ53.2,127.0,128.2,128.4,140.4ppm；MS(ESI,m/z):198(M+H+).

Claims (10)

1. The preparation method for synthesizing the amine compound by amide through the catalytic hydrosilylation of iridium and boron reagents is characterized by comprising the following steps: in an organic solvent, amide and silane react under the catalysis of an iridium complex and a boron reagent, and then amine is obtained through concentration and purification; the synthetic route is as follows:
Figure FDA0002682736350000011
wherein R is1And R2Selected from hydrogen, alkyl or aryl; r3Selected from hydrogen, alkyl, aryl or alkoxy; [ Ir ]]Is an iridium complex, [ B ]]Is a boron reagent and Si-H is silane.
2. The process according to claim 1 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, characterized by: the alkyl is selected from C1-C20, the aryl is selected from C6-C20, and the alkoxy is selected from C1-C7.
3. The process according to claim 1 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, characterized by: the molar ratio of the amide to the iridium complex to the boron reagent to the silane is 1: 0.0001-0.001: 0.01-0.05: 2-4.
4. The process according to claim 1 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, characterized by: the iridium complex packageIncluding IrCl (CO) (PPh)3)2。
5. The process according to claim 1 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, characterized by: the boron reagent comprises (C)6F5)3B。
6. The process according to claim 1 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, characterized by: the silane is selected from an alkoxysilane or an alkylsilane.
7. The process according to claim 6 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, wherein: the silane is selected from (EtO)3SiH、Et3SiH、PMHS、TMDS，Et2SiH2Or Ph2SiH2。
8. The process according to claim 1 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, characterized by: the organic solvent is selected from ether, halogenated hydrocarbon or aromatic hydrocarbon.
9. The process according to claim 8 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, wherein: the ether is selected from C2-C6 ether, and the halogenated hydrocarbon is selected from C1-C6 halogenated hydrocarbon.
10. The process according to claim 8 for the synthesis of amines by amide hydrosilation catalyzed by iridium and boron reagents, wherein: the organic solvent is selected from tetrahydrofuran, 2-methyltetrahydrofuran, dichloromethane, dichloroethane, toluene or xylene.
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Publication number Priority date Publication date Assignee Title
CN111484385A (en) * 2019-01-28 2020-08-04 中国科学院上海有机化学研究所 Hydrosilylation reaction method for catalyzing amide by organic boron and inorganic base

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Publication number Priority date Publication date Assignee Title
CN111484385A (en) * 2019-01-28 2020-08-04 中国科学院上海有机化学研究所 Hydrosilylation reaction method for catalyzing amide by organic boron and inorganic base

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* Cited by examiner, † Cited by third party
Title
RYAN C. CHADWICK等: "Metal-Free Reduction of Secondary and Tertiary N‑Phenyl Amides by Tris(pentafluorophenyl)boron-Catalyzed Hydrosilylation", 《J. ORG. CHEM. 》 *
TATIANA ROGOVA等: "Reverse Polarity Reductive Functionalization of Tertiary Amides via a Dual Iridium-Catalyzed Hydrosilylation and Single Electron Transfer Strategy", 《ACS CATAL.》 *
YANN CORRE等: "Efficient and selective hydrosilylation of secondary and tertiary amides using an iridium(III) metallacycle catalyst: development and mechanistic investigation", 《CHEMCATCHEM》 *

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