A mild method for protodesilylation of α-dimethylphenylsilyl ester substrates

Abstract

Mild conditions (1.2 eq. Hg(OAc)2, 1.2 eq. TBAF in 1:1 MeOH/THF; 35 min at 0 °C) have been developed for the protodesilylation of α- dimethylphenylsilyl esters. An enolate-dependent mechanism for the reaction was supported through studies indicating the clean incorporation of deuterium. To further investigate the mechanism, the optimal conditions as well as the kinetics of the reaction were explored.