氮、硫双齿配体-钯促进的Suzuki-Miyaura交叉偶联反应  

Suzuki-Miyaura Cross Coupling Reaction Promoted by Palladium Complex with N,S-Bidentate Ligand

作　　者：张占金 覃晴 唐霓 徐宁 韦敏雪 陈会英 ZHANG Zhan-jin;QIN Qing;TANG Ni;XU Ning;WEI Min-xue;CHEN Hui-ying(College of Life Science,Dalian Minzu University,Dalian 116605,China)

机构地区：[1]大连民族大学生命科学学院,辽宁大连116605

出　　处：《合成化学》2018年第12期895-899,共5页Chinese Journal of Synthetic Chemistry

基　　金：中央高校自主科研基金资助项目(DC201501020201)

摘　　要：钯配合物促进的Suzuki-Miyaura交叉偶联反应为构建碳-碳骨架的重要方法,主要用于药物化学、天然产物、材料学及超分子配体等领域。以2-噻吩甲醛、脂肪族/芳香族伯胺、取代肼及羟胺等为原料,合成了9种2-噻吩甲醛亚胺类N,S-双齿配体(3a～3i),其结构经1H NMR,13C NMR和HR-MS(APCI)表征。并以N-环己基-2-噻吩甲亚胺(3b)为例,研究了配体对钯促进的Suzuki-Miyaura交叉偶联反应的催化性能。结果表明:在反应体系Pd(OAc)2/3b/Cs2CO3/DMF中,苯硼酸与芳溴的交叉偶联反应的分离产率达到95%。Palladium-complex promoted Suzuki-Miyaura cross-coupling reactions were important channel for the formation of carbon-carbon framework in many fields such as pharmacochmistry,natural product,material science and supramolecular ligand.Nine bidentate N,S-ligands of2-thiophene formaldehyde imines(3a^3i)were synthesized through2-thiophene formaldehyde,aliphatic or aromatic primary amine,substituted hydrazine and azanol.The structures were characterized by^1H NMR,^13C NMR and HR-MS(APCI).N-cyclohexyl-2-thiophene methyl imine(3b)were applied to Suzuki-Miyaura coupling reactions promoted by palladium under moderate experimental condition.The results indicated that in the reaction system of Pd(OAc)2/3b/Cs2CO3/DMF,the yield of cross coupling reaction of aryl boric acid with aryl halides were up to95%.

关 键 词：2-噻吩甲醛 亚胺N S-双齿配体 苯硼酸 芳基溴 Suzuki-Miyaura交叉偶联反应 合成 

分 类 号：O643.32[理学—物理化学] O626[理学—化学]