有机化学 ›› 2017, Vol. 37 ›› Issue (9): 2250-2262.DOI: 10.6023/cjoc201704031 上一篇    下一篇

所属专题: 热点论文合辑

综述与进展

金属催化的共轭二烯的1,2-双官能化反应的研究进展

吴正兴, 张万斌   

  1. 上海交通大学化学化工学院 上海 200240
  • 收稿日期:2017-04-18 修回日期:2017-05-22 发布日期:2017-05-25
  • 通讯作者: 张万斌 E-mail:wanbin@sjtu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21232004,21672142)、上海市优秀学科带头人(No.14XD1402300)和上海市科委基础研究基金(No.15JC1402200)资助项目.

Recent Advances in Metal-Catalyzed 1,2-Difunctionalization of Conjugated Dienes

Wu Zhengxing, Zhang Wanbin   

  1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2017-04-18 Revised:2017-05-22 Published:2017-05-25
  • Contact: 10.6023/cjoc201704031 E-mail:wanbin@sjtu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21232004, 21672142), the Program of Shanghai Subject Chief Scientists (No. 14XD1402300) and the Basic Research Foundation of Shanghai Science and Technology Committee (No. 15JC1402200).

共轭二烯的1,2-双官能化反应是重要的均相催化反应之一.反应所得的双官能化产物广泛存在于天然产物和生物活性的化合物中,也是很多重要的有机中间体的来源;而且双官能化产物中还保留有一个可以继续转化的双键,可以更灵活地构建我们所需的目标结构,或继续官能化,从而实现简单二烯的多官能化反应,得到邻近的多官能化产物.此领域中主要的难点在于反应中区域选择性、化学选择性和立体选择性等复杂选择性的控制.近年来,随着金属有机化学的不断发展,已陆续实现了金属钯、铜、铁或银催化的共轭二烯的1,2-双官能化反应,而且有些报道中通过引入手性配体成功地实现了共轭二烯的不对称1,2-双官能化反应.本综述将对近年来金属催化的共轭二烯的1,2-双官能化反应的研究进展进行重点介绍.

关键词: 金属催化, 共轭二烯, 1,2-双官能化

The 1,2-difunctionalization of conjugated dienes is an important homogeneous catalytic reaction. The obtained products through 1,2-difunctionalization are widely existed in natural products and bioactive compounds, and are also sources of important organic intermediates, in addition, the preserved double bond in the difunctionalized product can be further transformed to give the desired structures or be functionalized sequentially to achieve multi-functionalization. The main difficulties focus on the encountered complex selectivities, including the regioselectivity, chemoselectivity and stereoselectivity in reactions. In recent years, with the development of organometallic chemistry, metal palladium, copper, iron or silver catalyzed 1,2-difunctionalizations of conjugated dienes have been reported in succession. In some cases the enantioselective 1,2-difunctionalizations of conjugated dienes were achieved via the introduction of chiral ligands. This review mainly focus on the recent metal catalyzed 1,2-difunctionalizations of conjugated dienes.

Key words: metal-catalyzed, conjugated diene, 1,2-difunctionalization