有机化学 ›› 2015, Vol. 35 ›› Issue (3): 522-527.DOI: 10.6023/cjoc201412041 上一篇    下一篇

研究专题

钯催化芳烃/烯烃与烯丙酯的氧化Heck交叉偶联反应的最新研究进展

尚筱洁a, 柳忠全b   

  1. a 甘肃农业大学资源与环境学院 兰州 730070;
    b 兰州大学功能有机分子化学国家重点实验室 兰州 730000
  • 收稿日期:2014-12-25 修回日期:2015-01-14 出版日期:2015-03-25 发布日期:2015-01-23
  • 通讯作者: 尚筱洁, 柳忠全 E-mail:liuzhq@lzu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21272096, 21472080)资助项目.

Recent Developments in Pd-Catalyzed Oxidative Heck Cross Coupling Reaction of Arenes/Alkenes with Allylic Esters

Shang Xiaojiea, Liu Zhongquanb   

  1. a College of Resources and Environment, Gansu Agricultural University, Lanzhou 730070;
    b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000
  • Received:2014-12-25 Revised:2015-01-14 Online:2015-03-25 Published:2015-01-23
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21272096, 21472080).

芳烃与烯烃通过两分子sp2-C—H键脱氢偶联, 构建多取代烯烃的反应称之为氧化Heck反应或脱氢Heck反应, 也叫Fujiwara-Moritani反应. 在过去的几十年里, 由于此类反应直接通过C—H键官能团化形成C—C键而备受关注. 然而, 绝大多数的此类转化只能适用于缺电子烯烃. 富电子烯烃如烯丙酯或烯丙醚类化合物参与的氧化Heck偶联很少被报道. 近几年来, 我们课题组以及其他研究小组发展了一些十分高效的钯催化芳烃/烯烃与烯丙酯/烯丙醚的氧化脱氢偶联新方法. 本文将概述这些有趣的、原子经济的氧化偶联反应的最新研究进展.

关键词: 钯催化, 氧化Heck反应, 烯丙酯, 碳氢活化, 碳碳键形成

The cross coupling reaction of arene with alkene generating substituted olefin through two sp2-C—H bond activation is named oxidative Heck reaction, dehydrogenative Heck reaction (DHR), or Fujiwara-Moritani reaction. In the past decades, these reactions have drawn much attention due to their C—C bond formations via direct C—H functionalization. However, only electron-deficient alkenes are effective coupling partners in most of these systems. The oxidative Heck reaction using electron-rich olefins such as allylic esters and ethers as the coupling partners has rarely been studied. Recently, several novel Pd-catalyzed strategies for cross coupling reactions of arenes/alkenes with allylic esters/ethers have been explored by us and other groups. This review will summarize the developments in this interesting and atom-economic area.

Key words: Pd-catalysis, oxidative Heck reaction, allylic ester, C—H activation, C—C bond formation