DOI: 10.1021/acs.joc.6c01316 ISSN: 0022-3263

Photo-Induced Three-Component Radical Trifluoromethylation/Heteroarylation of Alkenes via EDA Complexes

Zhijun Zhu, Xiaopeng Hai, Yuyu Lv, Ke-Hu Wang, Junjiao Wang, Bo-Sheng Zhang, Danfeng Huang, Yulai Hu

Abstract

This study develops a visible-light-induced electron donor–acceptor (EDA) complex strategy, employing the inexpensive and readily available DBU as the electron donor and the industrially available CF3Br as the trifluoromethyl source, to achieve the trifluoromethylation/heteroarylation of alkenes. This method offers advantages in cost-effectiveness and facile postreaction processing, without requiring transition metals or fluorescent dyes as photocatalysts. Moreover, nitrogen-containing heterocycles such as quinoxalinones, uracils, and pyrazines are all compatible in this transformation through C–H alkylation, providing a convenient and economical new avenue for the green late-stage modification of nitrogen-containing heterocyclic compounds.