Enhancing the Extent of Enolization for α‑C–H Bonds of Aliphatic Carboxylic Acid Equivalents via Ion Pair Catalysis: Application toward α‑Chalcogenation

In general, the α-functionalization of carboxylic acid derivatives requires either a transition metal catalyst or a stoichiometric activating agent/strong base/external additive. A transition metal free α-chalcogenation of aliphatic carboxylic acid equivalents is reported herein via ion pair formation using K3PO4 as a catalyst. Mild conditions, broad scope, scalability of the process, attaining bioactive glucokinase activators, and some synthetic intermediates establish merits of the strategy.