CN115466158B - 1, 3-triaryl-1, 3-butadiene derivative and synthesis method thereof - Google Patents

1, 3-triaryl-1, 3-butadiene derivative and synthesis method thereof Download PDF

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CN115466158B
CN115466158B CN202110648269.0A CN202110648269A CN115466158B CN 115466158 B CN115466158 B CN 115466158B CN 202110648269 A CN202110648269 A CN 202110648269A CN 115466158 B CN115466158 B CN 115466158B
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bromostilbene
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acetophenone
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CN115466158A (en
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林杰
余正坤
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Dalian Institute of Chemical Physics of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
    • C07C1/323—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Abstract

The invention discloses a 1, 3-triaryl-1, 3-butadiene derivative and a synthesis method thereof. O-bromostilbene and acetophenone p-toluenesulfonyl hydrazone are used as starting materials, a transition metal palladium salt is used as a catalyst, and under alkaline conditions, a 1, 3-butadiene skeleton is constructed in one step through 1, 4-palladium migration/soldier insertion/beta-hydrogen elimination, so that a series of 1, 3-triaryl-1, 3-butadiene derivatives are generated, and the obtained 1, 3-triaryl-1, 3-butadiene derivatives have potential aggregation-induced emission performance. The method has the advantages of easily available raw materials, simple and convenient operation, mild synthesis reaction conditions, high reaction efficiency and diversity of functional groups.

Description

1, 3-triaryl-1, 3-butadiene derivative and synthesis method thereof
Technical Field
The invention relates to a 1, 3-triaryl-1, 3-butadiene derivative and a synthesis method thereof, belonging to the technical field of chemical organic synthesis.
Background
The substituted 1, 3-diene is a common important synthetic block, and the 1, 3-triaryl-1, 3-butadiene derivative has potential aggregation-induced emission performance, so that efficient synthesis of 1, 3-triaryl-1, 3-butadiene is important. The current synthetic strategies include Heck reaction (chem. Eur. J.2013,19,3504), cross-coupling (RSC Advances.2014,4,39497), wittig double bond cleavage (RSC Advances.2020,10,35109), and the like. However, these methods have certain disadvantages, such as harsh reaction conditions, sensitive operation, complex synthesis steps, isomers of the product, and inability of the sensory energy group to be compatible with strongly basic organometallic reagents, and very limited application range of the substrate, so that it is still necessary to develop a one-step catalytic synthesis method for 1, 3-triaryl-1, 3-butadiene.
Disclosure of Invention
The invention aims at using o-bromostilbene II and acetophenone p-toluenesulfonyl hydrazone III which are easy to prepare, have structural diversity and high reaction efficiency as raw materials and adopting 1, 4-palladiumMigration/carbene insertion/beta-hydrogen elimination, one-step realization of 1, 3-butadiene skeleton construction, regulation and control of R in o-bromostilbene and acetophenone p-toluenesulfonyl hydrazone 1 、R 2 、R 3 Substituents, a series of 1, 3-triaryl-1, 3-butadiene derivatives of different structures with potential aggregation-induced emission properties are synthesized.
The invention provides a 1, 3-triaryl-1, 3-butadiene derivative, which has a molecular structural formula I as follows:
R 1 ，R 2 ，R 3 1-5 substituents selected from methyl, ethyl, tertiary butyl, methoxy, trifluoromethyl, fluoro, chloro, trifluoromethoxy and cyano.
The invention provides a synthesis method of a 1, 3-triaryl-1, 3-butadiene derivative I, which takes o-bromostilbene II as an initial raw material and takes transition metal palladium salt as a catalyst, and the raw material reacts with acetophenone p-toluenesulfonyl hydrazone III in a solvent under alkaline condition, and the 1, 3-triaryl-1, 3-butadiene derivative I is generated in one step through a 1, 4-palladium migration/carbene insertion/beta-hydrogen elimination process.
The molecular structural formula of the o-bromostilbene II is as follows:
R 1 ，R 2 1-5 substituents selected from methyl, ethyl, tertiary butyl, methoxy, trifluoromethyl, fluoro, chloro, trifluoromethoxy and cyano, and the number of the substituents is 1-5;
the molecular structural formula of acetophenone p-toluenesulfonyl hydrazone III is as follows:
R 3 selected from the group consisting of armor1 to 5 of groups, namely ethyl, tertiary butyl, methoxy, trifluoromethyl, fluorine, chlorine, trifluoromethoxy and cyano, and 1 to 5 substituents are adopted;
the synthetic route is shown in the following reaction formula:
wherein: the transition metal palladium salt is selected from palladium chloride (PdCl) 2 ) Palladium acetate (Pd (OAc)) 2 ) Palladium tetraphenylphosphine (Pd (PPh) 3 ) 4 ) One or more than two of palladium trifluoroacetate and bis (triphenylphosphine) palladium dichloride, wherein the molar ratio of the o-bromostilbene II to the catalyst is 1:0.01-1:0.5;
the mol ratio of the o-bromostilbene II to the acetophenone p-toluenesulfonyl hydrazone III is 1:1-1:3;
the alkali is selected from lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, potassium phosphate, sodium acetate, potassium acetate, cesium acetate, potassium tert-butoxide, and lithium tert-butoxide t One or more than two of Buoli), wherein the molar ratio of the o-bromostilbene II to the alkali is 1:0.1-1:5;
the reaction solvent is selected from one or more than two of N, N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), benzotrifluoride, acetonitrile, toluene (PhMe), 1, 4-dioxane and Tetrahydrofuran (THF), and the molar concentration of the o-bromostilbene II in the reaction solvent is 0.05-1.0M;
the reaction atmosphere is one or more than two of air, oxygen, nitrogen and argon; the reaction time is 0.1-48 hours; the reaction temperature is 0-130 ℃.
Further, in the above technical scheme, the transition metal palladium salt is preferably PdCl 2 。
Further, in the above-mentioned technical scheme, the alkali used in the reaction is preferably t BuOLi。
Further, in the above-mentioned technical scheme, the reaction is preferably carried out under a nitrogen atmosphere.
Further, in the technical scheme, the optimal reaction time for the reaction of the o-bromostilbene II and the acetophenone p-toluenesulfonyl hydrazone III to generate I is 1-4 hours.
Further, in the above technical scheme, the optimal reaction temperature is 40-80 ℃.
Further, in the above technical scheme, the reaction is preferably carried out in an aprotic polar solvent dimethyl sulfoxide.
Further, in the technical scheme, the preferable molar ratio of the o-bromostilbene II to the acetophenone p-toluenesulfonyl hydrazone III is 1:2.0.
Further, in the above technical scheme, the preferred molar ratio of the o-bromostilbene II to the catalyst (palladium salt) is 1:0.1.
Further, in the above technical scheme, the preferred molar ratio of the o-bromostilbene II to the base is 1:1-1:4, more preferably 1:2.0.
According to the invention, o-bromostilbene and acetophenone p-toluenesulfonyl hydrazone are used as starting materials, a transition metal palladium salt is used as a catalyst, and 1, 3-triaryl-1, 3-butadiene derivatives are generated in one step through 1, 4-palladium migration and carbene insertion processes under alkaline conditions. Compared with the reported method for synthesizing the 1, 3-triaryl-1, 3-butadiene derivative, the method only needs one-step reaction, has simple and convenient operation, mild condition, high synthesis reaction efficiency, 31-84 percent of yield, preferably 50-84 percent, and good regioselectivity and functional group diversity of the product. The 1, 3-triaryl-1, 3-butadiene synthesized by the invention has potential aggregation-induced emission performance, and the skeleton structure can be used as a synthetic block of medicines and various chemical product structures.
The invention has the following advantages:
1) The synthons o-bromostilbene II and acetophenone p-toluenesulfonyl hydrazone III have structural diversity and can be used for synthesizing 1, 3-triaryl-1, 3-butadiene derivatives I with different types and structures.
2) Synthon III is easy to prepare, low in cost and easy for industrial production.
3) Synthesis of 1, 3-triaryl-1, 3-butadiene derivative I using relatively low cost PdCl 2 As a catalyst.
4) The 1, 3-triaryl-1, 3-butadiene derivative I has high product yield up to 84% and only needs one step of 1, 3-butadiene skeleton construction.
5) The synthesis reaction condition of the 1, 3-triaryl-1, 3-butadiene derivative I is milder, and the temperature is 40-80 ℃.
6) The 1, 3-triaryl-1, 3-butadiene derivative I product has good stereoselectivity, functional group diversity and wide application.
In a word, the invention utilizes the structural diversity and multiple reaction centers of the o-bromostilbene II and the acetophenone p-toluenesulfonyl hydrazone III to efficiently synthesize the 1, 3-triaryl-1, 3-butadiene derivatives I with different types and structures, the raw materials are cheap and easy to obtain, only one-step reaction is needed to obtain a series of 1, 3-triaryl-1, 3-butadiene derivative structures, the operation is simple and convenient, the condition is mild, and the yield of target products is high.
Detailed Description
Under nitrogen, in tetrahydrofuran solvent, o-bromodiphenyl ketone A reacts with methyl triphenyl phosphonium bromide B to generate o-bromodiphenyl ethylene II. R in A 1 、R 2 Wherein the definition is as in formula II.
The specific process is as follows: methyl triphenyl phosphonium bromide B (10.0 mmol) and potassium t-butoxide (16.5 mmol) were added to the reaction flask, 10mL of tetrahydrofuran was added under nitrogen, a solution of o-bromobenzophenone a (2.0 mmol) in tetrahydrofuran (1M) was slowly added dropwise at room temperature, and the reaction was stirred at room temperature overnight. The mixture was quenched with saturated ammonium chloride solution, extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the volatile components were removed under reduced pressure, followed by column chromatography over silica gel (eluent petroleum ether (60-90 ℃)/ethyl acetate, v/v=50:1) to give the desired product II. The target product is confirmed by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.
Raw material 2a of the following example was prepared by the following literature method:
Q.N.Wang,R.J.Chen,J.Lou,D.H.Zhang,Y.G.Zhou,and Z.K.Yu,ACS Catal.2019,9,11669-11675.
in ethanol solution, acetophenone C reacts with p-toluenesulfonyl hydrazine D to generate acetophenone p-toluenesulfonyl hydrazone III. RR in C 3 Wherein the definition is as in formula III.
The specific process is as follows: to a 100mL single vial was added acetophenone (10 mmol), tsNHNH 2 (10 mmol,1.8623 g), ethanol 50mL, reflux at 65℃for 2h. Taking out the magneton after stopping the reaction, concentrating under reduced pressure to about 20mL, and cooling and crystallizing in a refrigerator. And (3) after recrystallization, carrying out suction filtration, washing by PE, and drying to obtain a target product white solid III. The target product was confirmed by nuclear magnetic resonance spectroscopy.
The following examples of starting materials 3a, 3b were prepared by the following literature methods:
F.Huang,Z.Q.Liu,Q.N.Wang,J.Lou,Z.K.Yu,Org.Lett.2017,19,3660-3663.
the present invention will be further understood by the following examples, but the content of the present invention is not limited thereto.
Example 1
In a glove box, pdCl is weighed in turn 2 (0.03mmol)， t BuLi (0.6 mmol), acetophenone p-toluenesulfonyl hydrazone 3a (0.6 mmol), N 2 O-bromobenzophenone 2a (0.3 mmol) was added thereto, and the mixture was put into an oil bath at 60℃for 2 hours with 3mL of dimethyl sulfoxide. After the completion of the reaction, the mixture was cooled to room temperature, and then separated by silica gel column chromatography (eluent petroleum ether (60-90 ℃)/ethyl acetate, v/v=50:1) to give the objective product 1a (67 mg, yield 79%) as a colorless liquid. The target product was confirmed by nuclear magnetic resonance spectroscopy.
Data on characterization of the Compounds
1, 3-triphenyl-1, 3-butadiene derivative (1 a), colorless liquid. 1 H NMR(400MHz,CDCl 3 )δ7.40(dd,J＝7.7,2H,1.2Hz),7.33(m,5H),7.19(m,8H),6.76(s,1H),5.41(s,1H),5.05(s,1H). 13 C{ 1 H}NMR(100MHz,CDCl 3 )δ145.43,144.82,143.25,140.87,140.20,130.26,128.46,128.31,128.22,128.09,128.05,127.73,127.53,127.16,126.82,117.49.
Example 2
In a glove box, pdCl is weighed in turn 2 (0.03mmol)， t BuLi (0.6 mmol), 4-bromoacetophenone p-toluenesulfonylhydrazone 3b (0.6 mmol), N 2 O-bromobenzophenone 2a (0.3 mmol) was added thereto, and the mixture was put into an oil bath at 60℃for 2 hours with 3mL of dimethyl sulfoxide. After the completion of the reaction, the mixture was cooled to room temperature, and then separated by silica gel column chromatography (eluent petroleum ether (60-90 ℃)/ethyl acetate, v/v=50:1) to give the desired product 1b (79 mg, yield 83%) as a white solid. The target product was confirmed by nuclear magnetic resonance spectroscopy.
Data on characterization of the Compounds
1, 1-diphenyl-3-p-chlorophenyl-1, 3-butadiene derivative (1 b), white solid. 1 H NMR(400MHz,CDCl 3 )δ7.35(m,7H),7.19(m,7H),6.79(s,1H),5.43(s,1H),5.17(s,1H). 13 C{ 1 H}NMR(100MHz,CDCl 3 )δ145.19,144.60,143.02,139.94,139.25,133.16,130.22,128.33,128.22,128.17,128.09,128.04,127.89,127.87,127.29,118.15.
Example 3
The reaction procedure and operation were as in example 1, except for 2a and PdCl 2 The molar ratio of (2) is 1:0.05. The reaction was stopped, and the desired product 1a (38 mg, yield 45%) was obtained by working up.
Example 4
The procedure and operation were as in example 1, except that DMSO was replaced with THF. The reaction was stopped, and the desired product 1a (50 mg, yield 60%) was obtained by working up.
Example 5
The reaction procedure and operation were as in example 1, except that DMSO was changed to PhMe. The reaction was stopped, and the desired product 1a (40 mg, yield 47%) was obtained by working up.
Example 6
The reaction procedure and operation were as in example 1, except that PdCl was used in the following manner 2 Pd (PPh) is changed into 3 ) 4 . The reaction was stopped, and the desired product 1a (35 mg, yield 41%) was obtained by working up.
Example 7
The reaction procedure and operation were as in example 1, except that PdCl was used in the following manner 2 Pd (OAc) instead 2 . The reaction was stopped, and the desired product 1a (26 mg, yield 31%) was obtained by working up.
Example 8
The reaction procedure and operation were as in example 1, except that N 2 Change to O 2 . The reaction was stopped, and the desired product 1a (30 mg, yield 35%) was obtained by working up.
Example 9
The reaction procedure and operation were as in example 1, except that N 2 Instead of air. The reaction was stopped, and the desired product 1a (37 mg, yield 43%) was obtained by working up.
Example 10
The reaction procedure and operation were the same as in example 1, except that the temperature of 60℃was changed to 40 ℃. The reaction was stopped, and the desired product 1a (42 mg, yield 50%) was obtained by working up.
The method has the advantages of easily obtained raw materials, simple and convenient operation, mild synthesis reaction conditions, high reaction efficiency and diversity of functional groups.

Claims (7)

1. A synthesis method of 1, 3-triaryl-1, 3-butadiene derivatives is characterized in that: o-bromostilbene II is used as a starting material, a transition metal palladium salt is used as a catalyst, and reacts with acetophenone p-toluenesulfonyl hydrazone III in a solvent under an alkaline condition to generate 1, 3-triaryl-1, 3-butadiene derivative I in one step;
the molecular structural formula of the o-bromostilbene II is as follows:
R 1 ，R 2 each independently selected from hydrogen, methyl, ethyl, tertiary butyl, methoxy, trifluoromethyl, fluorine, chlorine, trifluoromethoxy and cyano, and the number of substituents is 1-5;
the molecular structural formula of acetophenone p-toluenesulfonyl hydrazone III is as follows:
R 3 1-5 substituents selected from methyl, ethyl, tertiary butyl, methoxy, trifluoromethyl, fluoro, chloro, trifluoromethoxy and cyano, and the number of the substituents is 1-5;
the synthetic route is shown in the following reaction formula:
2. the synthesis method according to claim 1, wherein:
the transition metal palladium salt is selected from one or more than two of palladium chloride, palladium acetate, tetraphenylphosphine palladium, trifluoroacetate and ditriphenylphosphine palladium dichloride, and the molar ratio of the o-bromostilbene II to the catalyst is 1:0.01-1:0.5;
the mol ratio of the o-bromostilbene II to the acetophenone p-toluenesulfonyl hydrazone III is 1:1-1:3;
the alkali is selected from one or more of lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, potassium phosphate, sodium acetate, potassium acetate, cesium acetate, potassium tert-butoxide and lithium tert-butoxide, and the molar ratio of the o-bromostilbene II to the alkali is 1:0.1-1:5;
the reaction solvent is selected from one or more than two of N, N-dimethylformamide, dimethyl sulfoxide, benzotrifluoride, acetonitrile, toluene, 1, 4-dioxane and tetrahydrofuran, and the molar concentration of the o-bromostilbene II in the reaction solvent is 0.05-1.0M;
the reaction atmosphere is one or more than two of air, oxygen, nitrogen and argon; the reaction time is 0.1-48 hours; the reaction temperature is 0-130 ℃.
3. The synthesis method according to claim 2, characterized in that: the molar ratio of the o-bromostilbene II to the catalyst is 1:0.01.
4. The synthesis method according to claim 2, characterized in that: the molar ratio of the o-bromostilbene II to the acetophenone p-toluenesulfonyl hydrazone III is 1:2.0.
5. The synthesis method according to claim 2, characterized in that: the molar ratio of the o-bromostilbene II to the alkali is 1:1-1:4.
6. The synthesis method according to claim 2, characterized in that: the reaction time is 1-4 hours.
7. The synthesis method according to claim 2, characterized in that: the reaction temperature is 40-80 ℃.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112209812A (en) * 2019-07-11 2021-01-12 中国科学院大连化学物理研究所 1, 1-diaryl-2-alkyl ethylene derivative and synthetic method thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112209812A (en) * 2019-07-11 2021-01-12 中国科学院大连化学物理研究所 1, 1-diaryl-2-alkyl ethylene derivative and synthetic method thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Oeser, Petr 等.Formation of trisubstituted buta-1,3-dienes and a,b-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents.RSC Advances.2020,第10卷(第58期),35109-35120. *
Synthesis of Conjugated Dienes and Polyenes via Diethyl Phosphite Promoted Carbonyl Olefination;Wang, Ru 等;RSC Advances;第4卷(第74期);39497-39507 *

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