A new class of substrates for nucleophilic 5-endo-trig cyclization, 2-trifluoromethyl-1-alkenes: synthesis of five-membered hetero- and carbocycles that bear fluorinated one-carbon units

Chemistry, an Asian Journal
Junji IchikawaMasahiro Ikeda

Abstract

Disfavored 5-endo-trig cyclizations were achieved in 2-trifluoromethyl-1-alkenes with a nucleophilic nitrogen, oxygen, sulfur, or carbon atom through 1) intramolecular S(N)2' reaction with loss of a fluoride ion or 2) intramolecular nucleophilic addition to the vinylic group. This reaction manifold provides a versatile method for the synthesis of indolines, indoles, pyrrolidines, tetrahydrofurans, 2,3-dihydrobenzo[b]thiophenes, tetrahydrothiophenes, and cyclopentanes that bear a fluorinated one-carbon unit such as a difluoromethylene, difluoromethyl, or trifluoromethyl group.

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Citations

Oct 16, 2015·Organic Letters·Yu-Tao HeYong-Min Liang
Jun 23, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Tetsuhiro Nemoto
Aug 21, 2018·Chemical Communications : Chem Comm·Jean-Denys Hamel, Jean-François Paquin
Oct 8, 2019·Chemical Communications : Chem Comm·Pei FanChuan Wang
Jul 23, 2021·Journal of the American Chemical Society·Chang ZhangChuan Wang
Feb 21, 2014·Organic Letters·Takeshi FujitaJunji Ichikawa

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