有机化学 ›› 2017, Vol. 37 ›› Issue (2): 284-300.DOI: 10.6023/cjoc201607035 上一篇    下一篇

综述与进展

金属催化的碳-杂键对炔键的加成反应研究进展

赵飞a, 贾秀稳a, 王东萍a, 费朝丽a, 吴成林b,c, 王江b,c, 柳红b,c   

  1. a 成都大学四川抗菌素工业研究所 抗生素研究与再评价四川省重点实验室 成都 610052;
    b 中国科学院上海药物研究所 受体结构与功能重点实验室 上海 201203;
    c 中国科学院大学 北京 100049
  • 收稿日期:2016-07-21 修回日期:2016-10-14 发布日期:2016-11-03
  • 通讯作者: 柳红 E-mail:hliu@mail.shcnc.ac.cn
  • 基金资助:

    国家自然科学基金(Nos.21602022,21372235)和抗生素研究与再评价四川省重点实验室开放课题(No.ARRLKF15-01)资助项目.

Research Progress in Metal-Catalyzed Addition of Carbon-Hetero Bonds to Alkynes

Zhao Feia, Jia Xiuwena, Wang Dongpinga, Fei Chaolia, Wu Chenglinb,c, Wang Jiangb,c, Liu Hongb,c   

  1. a Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, Chengdu 610052;
    b Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
    c University of Chinese Academy of Sciences, Beijing 100049
  • Received:2016-07-21 Revised:2016-10-14 Published:2016-11-03
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21602022, 21372235) and the Open Project Program of Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province (No. ARRLKF15-01).

碳-杂键对炔键的加成反应已经成为对碳碳叁键进行官能团化的一种重要手段,此类反应可以一步快速构建两个化学键即一个碳-碳键和一个碳-杂键,因而具有反应效率高、原子经济性高的特点.近年来,Al,Fe,Ni,Cu,Ga,Ru,Rh,Pd,Hf,Ir,Pt,Au,Bi等催化的诸多类型的碳-杂键对炔键的加成反应取得了重要进展.根据对炔键进行加成的碳-杂键的类型分为C-H,C-B,C-N,C-O,C-Si,C-S,C-X(X=Cl,Br,I),C-Se键这8类逐一进行介绍,并对各类加成反应的反应条件、反应选择性(区域选择性和立体化学选择性)以及反应机理进行了讨论和总结.

关键词: 金属催化, 碳-杂键, 炔, 加成反应

The addition of carbon-hetero bonds to alkynes has become an important apporach for the functionalization of carbon-carbon triple bonds. It can construct two bonds, namely one carbon-carbon bond and one carbon-hetero bond, in a single one step. These addition reactions feature high efficiency and high atom-economy. In recent years, metal-catalyzed (Al, Fe, Ni, Cu, Ga, Ru, Rh, Pd, Hf, Ir, Pt, Au, Bi, etc.) addition of many various kinds of carbon-hetero bonds to alkynes has achieved lots of important developments. According to the types of carbon-hetero bonds, the addition of 8 different kinds of carbon-hetero bonds [C-H, C-B, C-N, C-O, C-Si, C-S, C-X (X=Cl, Br, I), C-Se] to alkynes is reviewed in this paper, and the reaction conditions, reaction selectivities (regioselectivities and stereoselectivities) and reaction mechanisms are also discussed and summarized.

Key words: metal-catalyzed, carbon-hetero bonds, alkynes, addition reactions