Citation: 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]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1727-1734. doi: 10.6023/cjoc201901047 shu

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

Corresponding author: Liu Yingjie, liuyj691@nenu.edu.cn Liang Deqiang, liangdq695@nenu.edu.cn
Received Date: 28 January 2019
Revised Date: 12 March 2019
Available Online: 2 June 2019
Fund Project: 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)the National Natural Science Foundation of China 21702083the Innovation Talents Foundation of Harbin of China 2015RAQXJ061the Program of Young Innovators of Education Department of Heilongjiang Province UNPYSCT-2016181

Figures(1)

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.
- unactivated alkenes,
- polychloromethylation,
- indolines,
- radical reaction
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