Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp(3) C-H cleavage.

Abstract

A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp(3) C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.