水溶性Salen-Pd配合物纯水相中催化Suzuki-Miyaura反应  

Water-soluble Salen-Pd complex catalyzed Suzuki-Miyaura reaction in pure water

作　　者：刘洋[1] 刘亚帅 刘岩[1] 刘平[1] 马晓伟[1] 薛梅[1] LIU Yang LIU Yashuai LIU Yan LIU Ping MA Xiaowei XUE Mei(School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi, Xinjiang 832003,Chin)

机构地区：[1]石河子大学化学化工学院/新疆兵团化工绿色过程重点实验室,新疆石河子832003

出　　处：《石河子大学学报（自然科学版）》2017年第2期231-235,共5页Journal of Shihezi University(Natural Science)

基　　金：国家自然科学基金(21563025);石河子大学杰出青年科技人才培育计划(2014ZRKXJQ05);石河子大学青年启动基金计划(RCZX201408)项目

摘　　要：联芳烃类化合物作为一种重要的结构单元,在天然产物、医药中间体、农药和液晶等方面的应用广泛,过渡金属钯催化的Suzuki-Miyaura偶联反应是构建芳基碳-碳键的重要方法之一,发展纯水相中钯催化C-C偶联具有重要的理论意义和应用价值。本文设计合成了一种水溶性好、结构稳定的Salen-Pd配合物,并将其应用于纯水相中催化Suzuki-Miyaura反应,实现了芳基C-C键的有效构建;邻位带有空间位阻的底物(溴代芳烃或芳基硼酸)都能够顺利的发生偶联反应,反应产率在中等和优秀之间;最佳催化反应条件为:溴代芳烃(0.5 mmol),芳基硼酸(0.75 mmol),三乙胺(1.0 mmol),Salen-Pd配合物(1 mol%),H2O(1.0 m L),反应温度100℃,反应时间3 h。该体系具有反应条件温和,底物适用范围广,原料廉价易得,不需要任何的有机溶剂、表面活性剂或相转移催化剂等优点。Biaryl units as important building blocks have been fo und in natural products, pharmaceutical intermediates, pesticides, and liquid crystals. Palladium-catalyzed Suzuki-Miyaura coupling reaction is one of the most important methods for the formation of Caryl-Caryl bond. Water has gained wide attention for it is cheap, readily available, non-corrosive, non-flammable and non-toxic. Therefore, it is necessary to develop an efficient system for facilitating this coupling reaction in pure water. In this paper, a water-soluble salen-Pd complex was synthesized and used as efficient catalysts for the Suzuki-Miyaura reactions in pure water. Notably, the reactions of substrates with sterically demanding ortho substituents （aryl bromides and/or arylboronic acids） proceed smoothly to generate corresponding products with moderate to high yields. The optimal reaction conditions were as follows： aryl bromide （0.5 mmol）, arylboronic acid （0.75 mmol）, EhN （1.0 mmol） as base, salen-Pd complex （1 mol%）, H20 （1.0 mL） as solvent, reaction temperature 100 ~C ,reaction time 3 h. Importantly, the catalytic system has the wide substrate scope and the high tolerance to various functional groups. Moreover, the system was carried out in the absence of any organic solvent, surfactant, or phase transfer agent.

关 键 词：钯催化 Suzuki-Miyaura反应 联苯化合物 水 

分 类 号：O625.13[理学—有机化学]