Synthesis of Polychloromethyl-Containing Indolines via Metal-Free Radical Arylpolychloromethylation of Unactivated Alkenes

doi:10.6023/cjoc201901047

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1727-1734.DOI: 10.6023/cjoc201901047 Previous Articles Next Articles

Special Issue: 金属有机化学

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无金属催化非活化烯烃的多氯甲基化/芳基化自由基反应合成含多氯甲基吲哚啉

李文兰^a, 孙一茼^b, 姚永超^b, 许颖^a, 李鹏^c, 刘颖杰^a, 梁德强^b

a 哈尔滨商业大学生命科学与环境科学研究中心哈尔滨 150076;
b 昆明学院化学科学与技术系昆明 650214;
c 黑龙江护理高等专科学校哈尔滨 150000

收稿日期:2019-01-28 修回日期:2019-03-12 发布日期:2019-04-08
通讯作者: 刘颖杰, 梁德强 E-mail:liuyj691@nenu.edu.cn;liangdq695@nenu.edu.cn
基金资助:
国家自然科学基金（No.21702083）、云南省高校科技创新团队支持计划、黑龙江省创新人才项目（No.UNPYSCT-2016181）、哈尔滨创新人才（No.2015RAQXJ061）资助项目.

Synthesis of Polychloromethyl-Containing Indolines via Metal-Free Radical Arylpolychloromethylation of Unactivated Alkenes

Li Wenlan^a, Sun Yitong^b, Yao Yongchao^b, Xu Ying^a, Li Peng^c, Liu Yingjie^a, Liang Deqiang^b

a Research Center on Life Sciences and Environmental Sciences, Harbin University of Commerce, Harbin 150076;
b Department of Chemistry, Kunming University, Kunming 650214;
c Heilongjiang Nursing College, Harbin 150000

Received:2019-01-28 Revised:2019-03-12 Published:2019-04-08
Contact: 10.6023/cjoc201901047 E-mail:liuyj691@nenu.edu.cn;liangdq695@nenu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21702083), the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province, the Program of Young Innovators of Education Department of Heilongjiang Province (No. UNPYSCT-2016181), and the Innovation Talents Foundation of Harbin of China (No. 2015RAQXJ061).

1. Synthesis of Polychloromethyl-Containing Indolines via Metal-Free Radical Arylpolychloromethylation of Unactivated Alkenes.PDF(11542KB)

Abstract

A metal-free polychloromethylation/cyclization cascade of N-allyl anlines is presented, which provides an access to polychloromethyl-substituted indolines with unactivated alkenes as radical acceptors and dicumyl peroxide (DCP) as the initiator. The inexpensive solvents of polychoromethanes (i.e., CH₂Cl₂, CHCl₃ and CCl₄) were used in the reaction as di-or trichloromethylating agents. This work has advantages of easy operation, mild conditions, low cost, and broad substrate scope.

Key words: unactivated alkenes, polychloromethylation, indolines, radical reaction

Cite this article

Li Wenlan, Sun Yitong, Yao Yongchao, Xu Ying, Li Peng, Liu Yingjie, Liang Deqiang. Synthesis of Polychloromethyl-Containing Indolines via Metal-Free Radical Arylpolychloromethylation of Unactivated Alkenes[J]. Chin. J. Org. Chem., 2019, 39(6): 1727-1734.

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无金属催化非活化烯烃的多氯甲基化/芳基化自由基反应合成含多氯甲基吲哚啉

Synthesis of Polychloromethyl-Containing Indolines via Metal-Free Radical Arylpolychloromethylation of Unactivated Alkenes

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