Synthesis of α-Hydroxy Carboxylic Acids via a Nickel(II)-Catalyzed Hydrogen Transfer Process

A new catalytic system for beta-alkylation of lactic acid with primary alcohols has been developed. In the presence of nickel(II) acetate tetrahydrate [Ni(OAc)(2)(H(2)O)(4)] and base, lactic acid reacts with primary alcohols to afford the corresponding coupled alpha-hydroxy carboxylic acids in good to excellent yields via a hydrogen transfer process without any hydrogen acceptor or hydrogen donor.