有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2211-2217.DOI: 10.6023/cjoc201903065 上一篇    下一篇

所属专题: 陈茹玉先生诞辰100周年

研究论文

钯催化溴代酚的[2+2+1]去芳构螺环化反应

李锟雨, 白璐, 栾新军   

  1. 西北大学化学与材料科学学院 西安 710127
  • 收稿日期:2019-03-28 修回日期:2019-04-26 出版日期:2019-08-25 发布日期:2019-05-28
  • 通讯作者: 白璐, 栾新军 E-mail:xluan@nwu.edu.cn;bailu@nwu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21672169)、西安市有机分子工程重点实验室(No.201805058ZD9CG42)资助项目.

Pd-Catalyzed Dearomative Spirocyclization of Bromophenols via[2+2+1] Strategy

Li Kunyu, Bai Lu, Luan Xinjun   

  1. College of Chemistry & Materials Science, Northwest University, Xi'an 710127
  • Received:2019-03-28 Revised:2019-04-26 Online:2019-08-25 Published:2019-05-28
  • Contact: 10.6023/cjoc201903065 E-mail:xluan@nwu.edu.cn;bailu@nwu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21672169), and the Key Laboratory Project of Xi'an City (No. 201805058ZD9CG42).

在零价钯的催化作用下,以简单且商品化的溴代苯酚为研究目标,炔烃作为偶联片段,通过[2+2+1]反应策略,实现了苯酚的去芳构螺环化转化,合成了一系列新颖的含有季碳中心的螺环骨架化合物.该方法采用的底物简单易得,具有宽泛的底物范围,并且可以获得较优的收率;在非对称炔烃方面,能以优异的区域选择性(>19∶1 rr)实现这一转化,极大地拓宽了苯酚去芳构化的研究范围.

关键词: 过渡金属催化, 去芳构化, 螺环化, 溴代酚

A novel palladium(0)-catalyzed dearomative spirocyclization reaction of bromophenols has been developed for building a series of spirocyclic architectures containing a quaternary carbon center via[2+2+1] strategy. This method employs inexpensive bromophenols and easily accessible alkynes. It exhibits a broad substrate scope in good yields. Notably, this transformation can be realized with high regioselectivity (>19:1 rr) when using unsymmetrical alkynes, which greatly expands the research scope of phenol dearomatization.

Key words: transition-metal-catalyzed, dearomatization, spirocyclization, bromophenols