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2022 , Vol. 42 >Issue 7: 2000 - 2014

DOI: https://doi.org/10.6023/cjoc202202028

综述与进展

配位导向下烯基同碳位C—H官能团化反应进展

  • 王亚洲 ,
  • 祝宇航 ,
  • 徐丽霞 ,
  • 贺瑞 ,
  • 张坚
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  • a中国石油化工股份有限公司胜利油田分公司 纯粱采油厂 山东滨州 256600
    b杭州师范大学材料与化学化工学院 有机硅化学及材料技术教育部重点实验室 杭州 311121
    c杭州师范大学 杭州师范大学附属医院 杭州 310015

收稿日期: 2022-02-23

  修回日期: 2022-03-23

  网络出版日期: 2022-04-11

基金资助

浙江省自然科学基金(LY19B020006); 杭州市口腔医学重点学科资助项目

收起

Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization

  • Yazhou Wang ,
  • Yuhang Zhu ,
  • Lixia Xu ,
  • Rui He ,
  • Jian Zhang
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  • aChunliang Oil Prod Plant, Shengli Oilfield, China Petro-Chemical Corporation, Binzhou, Shandong 256600
    bCollege of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121
    cDepartment of Stomatology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou 310015
* E-mail: ;

Received date: 2022-02-23

  Revised date: 2022-03-23

  Online published: 2022-04-11

Supported by

Natural Science Foundation of Zhejiang Province(LY19B020006); Key Subject of Stomatology in Hangzhou City

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摘要

配位导向下烯基C—H官能团化是制备多取代烯烃的常用方法, 反应通常经历弱配位基团(羟基、酰胺、羧酸、胺基等)协助下的双键在环内的金属杂环中间体(endo-metallocycle), 实现导向基邻碳位C—H官能团化, 表现出了优异的Z/E选择性, 目前发展的C—H官能团化类型丰富, 包括烯基化、烷基化、芳基化、炔基化、烯丙基化、杂原子化和多米诺环化等. 相比较而言, 导向基同碳位烯基C—H官能团化则发展缓慢, 可能是该反应需要经历更加不稳定的双键在环外的金属杂环中间体(exo-metallocycle), 严重阻碍了烯烃的配位C—H活化的发展. 近年来, 若干课题组在这方面报道了导向基同碳位烯基C—H官能团化, 包括烯基化、烯丙基化、芳基化、碘代、炔基化反应. 按C—H官能化类型介绍了配位导向下同碳位烯基C—H官能团化反应的研究进展, 并对该领域的发展前景进行了总结与展望.

关键词： 过渡金属催化; 烯烃; 导向基; 同碳位; 邻碳位; C—H官能团化

本文引用格式

王亚洲 , 祝宇航 , 徐丽霞 , 贺瑞 , 张坚 . 配位导向下烯基同碳位C—H官能团化反应进展[J]. 有机化学, 2022 , 42(7) : 2000 -2014 . DOI: 10.6023/cjoc202202028

Abstract

Vicinal group-directed alkenyl C—H functionalization provides general method toward the synthesis of multi- substituted alkenes, proceeding by the weakly coordination-group (such as hydroxyl, amide, carboxylic acid, amino group etc.) assisted endo-cyclometallation, leading to vicinal C—H functionalization with excellent E/Z selectivities, including alkenylation, alkylation, arylation, alkynylation, allylation, domino cyclization etc. In stark contrast, geminal group-directed alkenyl C—H functionalization attracted much less attentions presumably due to the difficult formation of exo-metallocyles, which greatly inhibited the development of directed alkenyl C—H functionalization. In recent years, several groups have demonstrated the importance of geminal group-directed alkenyl C—H functionalization, including alkenylation, arylation, alkynylation, allylation and iodination. The research progress is introduced according to the types of geminal C—H functionalization, and the reaction mechanisms and applications of specific reactions are discussed. The development prospects with outlook are also summarized

Key words： transition-metal-catalysis; alkenes; directing group; geminal; vicinal; C—H functionalization

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