Photoredox-mediated remote C(sp3)-H heteroarylation of free alcohols.

Affiliation

State Key Laboratory and Institute of Elemento-Organic Chemistry , College of Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email: [Email]

Abstract

We report an efficient and economical method for remote δ C(sp3)-H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis. The reaction sequence involves in situ alcoholysis of PFBI-OH with alcohol, generation of an alkoxy radical intermediate by SET reduction, 1,5-HAT, and Minisci-type C-C bond formation. This method uses a slight excess of alcohols, can facilitate reaction at δ methyl and methylene positions, and has been successfully applied to modification of complex drug molecules.