Metal-Free Visible-Light-Promoted Trifluoromethylation of Vinylcyclopropanes Using Pyrylium Salt as a Photoredox Catalyst

J Org Chem. 2019 Jul 5;84(13):8771-8781. doi: 10.1021/acs.joc.9b01033. Epub 2019 Jun 17.

Abstract

Visible-light-induced metal-free trifluoromethylation of activated, carbocyclic, and unactivated vinylcyclopropanes via a ring-opening reaction using the Langlois reagent (CF3SO2Na) is reported to synthesize allylic trifluoromethylated derivatives. Allylic trifluoromethylation was achieved by a photo-oxidative single electron transfer (SET) process at an ambient temperature and under metal-free conditions and visible-light irradiation using pyrylium salt as a photoredox catalyst. The reported methodology has an operational simplicity, broad substrate scope, high functional group tolerance, and scalability.

Publication types

  • Research Support, Non-U.S. Gov't