Photochemical akynylperfluoroalkylation of unactive alkenes mediated by halogen-bonded charge-transfer complexes

Abstract

We describe a catalyst-free visible-light mediated akynylperfluoroalkylation of unactive alkenes with perfluoroalkyl iodides, which provides a series of α-perfluoroalkyl-β-alkynyl ketone derivatives. This new synthetic protocol is enabled by a charge-transfer complex, which is a compound of a 1,4-enynol anion and an enolate ion of acetone as the electron donor and perfluoroalkyl iodides as the electron acceptor. Excellent functional group compatibility and chemoselectivity render this method suitable for fluoroalkylation of pharmaceutically relevant molecules, featuring a broad substrate scope, scalability and significant characteristics of green chemistry, further demonstrating the flexibility and potential for the synthesis of the mentioned compounds.