[1,2]-Retro-Brook Rearrangement Induced by Electrochemical Reduction of Silyl Enolates

Abstract Electrochemical reduction of the trimethylsilyl enolates of alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence of 1) single-electron reduction of the silyl enolate, 2) protonation with a phenol, 3) another single-electron reduction to form siloxy-substituted benzylic anion, and 4) the pivotal retro-Brook rearrangement.