锌促进的烯烃氢烷基化反应

doi:10.3969/j.issn.1000-1565.2017.04.006锌促进的烯烃氢烷基化反应

河北大学学报(自然科学版) ›› 2017, Vol. 37 ›› Issue (4): 364-368.DOI: 10.3969/j.issn.1000-1565.2017.04.006锌促进的烯烃氢烷基化反应

锌促进的烯烃氢烷基化反应

万晓龙, 陈衍炽,孙雨人,钱群

收稿日期:2016-12-10 出版日期:2017-07-25 发布日期:2017-07-25
通讯作者: 钱群(1968—),女,上海人,上海大学副教授,博士,主要从事有机合成研究. E-mail:qianqun@shu.edu.cn
作者简介:万晓龙(1983—),男,吉林农安人,上海大学在读博士研究生,主要从事有机合成研究. E-mail:wanxiaolong1983@163.com
基金资助:
国家自然科学基金面上项目(21372151)

Zinc promoted alkylation of olefins with hydrogen

WAN Xiaolong, CHEN Yanchi, SUN Yuren, QIAN Qun

School of Materials Science and Engineering, Shanghai University, Shanghai 200444, China

Received:2016-12-10 Online:2017-07-25 Published:2017-07-25

摘要/Abstract

摘要： 季全碳中心的构筑一直是有机合成中的难点和热点,其中以廉价三级溴代烷为原料,通过分子间C(sp³)—C(sp³)键形成来合成该类季全碳中心更是鲜有报道.采用廉价锌粉作为还原性自由基引发剂,诱导三级溴代烷形成叔碳自由基,进而实现用烯烃捕获该自由基的策略来高效构筑C(sp³)—C(sp³)键季全碳中心.

关键词: 还原偶联, C(sp³)—C(sp³)键, 锌

Abstract: The construction of the quaternary carbon center has been a difficult and hot issue in organic synthesis.In particular, the synthesis of quaternary carbon center by the formation of the intermolecular C(sp³)—C(sp³)bond with cheap tert-alkyl bromides is rarely reported.Recently, our group reported that nickel-catalyzed reductive coupling of aryl bromides with tertiary alkyl halides.Based on this, we proposed that using cheap reductive metal as a free radical initiator, mediated the formation of tertiary carbon free radicals from tert-alkyl bromides, and then the free radical captured by olefin to build C(sp³)—C(sp³)bond quaternary carbon center efficiently.Herein, we report the application of this strategy in constructing quaternary carbon center by Zn powder mediated reductive coupling reaction.

Key words: reductive coupling, C(sp³)—C(sp³)bonds, Zinc

中图分类号:

O621

万晓龙, 陈衍炽,孙雨人,钱群. 锌促进的烯烃氢烷基化反应[J]. 河北大学学报(自然科学版), 2017, 37(4): 364-368.

WAN Xiaolong, CHEN Yanchi, SUN Yuren, QIAN Qun. Zinc promoted alkylation of olefins with hydrogen[J]. Journal of Hebei University (Natural Science Edition), 2017, 37(4): 364-368.

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锌促进的烯烃氢烷基化反应

Zinc promoted alkylation of olefins with hydrogen

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