糖苷-氮杂环卡宾-钯-吡啶配合物及其高效催化水相Suzuki反应  

Synthesis of glucopyranoside-functionalized N-heterocyclic carbenes-Pd-pyridine complexes for efficient Suzuki reaction in water

作　　者：温小明[1,2] 王健 贺峦[1] 何鹏[2] 刘宇龙 周中高 WEN Xiao-ming;WANG Jian;HE Luan;HE Peng;LIU Yu-long;ZHOU Zhong-gao(Jiangxi College of Applied Technolgy,Ganzhou 341000,China;College of Chemistry and Chemical Engineering,Gannan Normal University,Ganzhou 341000,China)

机构地区：[1]江西应用技术职业学院,江西赣州341000 [2]赣南师范大学化学化工学院,江西赣州341000

出　　处：《化学研究与应用》2022年第5期1136-1144,共9页Chemical Research and Application

基　　金：国家自然科学基金项目(21562002)资助;江西省教育厅科学技术研究项目(GJJ201427,GJJ204902)资助;研究生创新基金项目(YCX20A008,YCX21A025)资助;大学生创新创业训练计划项目(CX210052)资助。

摘　　要：以β-D-葡萄糖五乙酸酯为原料,通过三步反应制备了两种碳水化合物衍生的氮杂环卡宾钯络合物[Glu-(NHCs)PdBr_(2)(Py),1a和1b]。初步研究发现,在空气氛围下,含甲氧基聚乙二醇单元的钯络合物1a能高效地促进纯水中的Suzuki偶联反应,催化剂用量低至0.01 mol%,能高效催化溴代芳烃和含吸电子基的氯代芳烃与苯基硼酸偶联反应,以91~100%的产率获得联芳烃。催化数据显示,络合物1a中的乙二醚链不仅改善其水溶性,还与金属Pd中心有配位作用,对提高催化剂的催化活性和稳定性有一定贡献。Two glucopyranoside-functionalized N-heterocyclic carbenes-Pd-pyridine complexes[Glu-(NHCs)PdBr_(2)(Py),1a and 1b]were prepared by a three-step reaction usingβ-D-glucose pentaacetate as raw material.The designed Glu-(NHCs)PdBr_(2)(Py)had been used as high efficiency catalyst in Pd-catalyzed Suzuki reaction in water under air.Complex 1a was effective for the Suzuki reaction of phenylboronic acid with a range of aryl bromides and aryl chlorides containing electron withdrawing groups,the corresponding biaryls were obtained in 91~100%yields with 0.01 mol%catalyst loading.The ether-oxygen in complex 1a not only improved its water solubility,but also coordinated with the metal Pd center,which contributed to the improvement of catalytic performance and stability.

关 键 词：氮杂环卡宾 碳水化合物 钯络合物 水溶性催化剂 SUZUKI反应 

分 类 号：O629.1[理学—有机化学]