Synthesis of CF3CH2-Containing Indolines by Transition-Metal-Free Aryltrifluoromethylation of Unactivated Alkenes

Deqiang Liang; Qishan Dong; Penghui Xu; Ying Dong; Weili Li; Yinhai Ma

doi:10.1021/acs.joc.8b01861

Synthesis of CF₃CH₂-Containing Indolines by Transition-Metal-Free Aryltrifluoromethylation of Unactivated Alkenes

J Org Chem. 2018 Oct 5;83(19):11978-11986. doi: 10.1021/acs.joc.8b01861. Epub 2018 Sep 17.

Authors

Deqiang Liang^{1

2}, Qishan Dong¹, Penghui Xu¹, Ying Dong³, Weili Li², Yinhai Ma¹

Affiliations

¹ Department of Chemistry , Kunming University , Kunming 650214 , China.
² Yunnan Engineering Technology Research Center for Plastic Films , Kunming 650214 , China.
³ College of Chemistry, Chemical Engineering and Materials Science , Shandong Normal University , Jinan 250014 , China.

PMID: 30198264
DOI: 10.1021/acs.joc.8b01861

Abstract

With an unactivated double bond as the radical acceptor, allyl amines underwent a metal-free trifluoromethylation/cyclization cascade with CF₃SO₂Na (Langlois' reagent), affording CF₃CH₂-containing indolines and tetrahydroisoquinolines, whose practical syntheses are significant challenges. This protocol features mild conditions, low cost, and a broad substrate scope.

Publication types

Research Support, Non-U.S. Gov't