Room Temperature Hydroalkylation of Electron-Deficient Olefins: sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event

Abstract

A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.