Enhanced ester dechloroacetylation through transesterification with trimethoxyborane

Abstract

A new strategy to remove the chloroacetyl group using B(OMe)₃ and K₃PO₄ in the presence of organophosphine is described. The reaction was performed on O-AcCl-protected benzylic, aliphatic primary, aliphatic secondary, allyl, and propargyl alcohols and phenols to generate free alcohols and phenols in good to excellent yields. Synthetically valuable and sensitive functional groups such as bromo, carbonyl, and dioxol remained intact during the reaction. The control experiments and in situ¹H NMR and ¹¹B NMR tracking experiments were conducted to understand the reaction mechanism.