A Phosphonium Ylide as an Ionic Nucleophilic Catalyst for Primary Hydroxyl Group Selective Acylation of Diols

Abstract

Carbonyl-stabilized phosphonium ylides exhibit great utility in modern organic synthesis, and they are known as an ambident nucleophile at the carbonyl oxygen atom and at the α-carbon atom. However, they have found limited use as catalysts. We focused on the inherent nucleophilicity of the oxygen atom to develop an ionic nucleophilic catalysis, and the phosphonium ylide-catalyzed primary alcohol selective acylation of mixed diols with acid anhydrides has been demonstrated. Mechanistic studies revealed the behavior of a catalyst, which would contribute to the field of ylide chemistry.