镍催化苯并降冰片烯与内炔的不对称[2+2]环加成反应研究  

Nickel-catalyzed asymmetric[2+2]cycloaddition reactions of benzonorbornadienes with internal alkynes

作　　者：樊保敏 徐丽娟 杨帆 陆光富 刘月娥 周永云 FAN Bao-min;XU Li-juan;YANG Fan;LU Guang-fu;LIU Yue-e;Zhou Yong-yun(School of Chemistry and Environment,Yunnan Minzu University,Kunming 650500,China;School of Ethnic Medicine,Yunnan Minzu University,Kunming 650500,China)

机构地区：[1]云南民族大学化学与环境学院,云南昆明650500 [2]云南民族大学民族医药学院,云南昆明650500

出　　处：《云南民族大学学报（自然科学版）》2021年第5期459-470,共12页Journal of Yunnan Minzu University:Natural Sciences Edition

基　　金：国家自然科学基金(22061048,21572198);云南省中青年学术和技术带头人后备人才项目(202005AC160016);云南省教育厅科学研究基金(2019Y0197).

摘　　要：通过研究发现在过渡金属Ni(COD)2、手性配体(R)-SIPHOS-Ph-Mor和添加剂Bu 4NI作为共催化体系,可以催化苯并降冰片烯类化合物与内炔发生不对称[2+2]环加成反应,最终合成一系列含有环丁烯结构的手性化合物,最高收率达到91%,最高ee值为92%.该催化体系对多种取代基的苯并降冰片烯类化合物及芳基炔烃都具有良好的适用性.In the catalytic system of Ni(COD)2 and chiral ligand(R)-SIPHOS-Ph-Mor,the addition of tetrabutylammonium iodide as additive can catalyze the asymmetric[2+2]cycloaddition reaction between benzonorbornadienes and internal alkynes,and finally synthesize a series of chiral compounds containing cyclobutene structures.The highest yield was 91%and the highest ee was 92%.The catalytic system is suitable for a variety of benzonorbornadienes with substituents and arylalkynes.

关 键 词：苯并降冰片烯 内炔 Ni(COD)2 [2+2]环加成反应 

分 类 号：O622[理学—有机化学]