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 K 3 PO 4 as a catalyst. Mild conditions, broad scope, scalability of the process, attaining bioactive glucokinase activators, and some synthetic intermediates establish merits of the strategy.
Benzoxazoles and benzothiazoles govern the PdII-catalyzed regiospecific methoxylation of the proximal-selective α-C(sp3)–H bond to access α-methoxyacetic acids and O-methylated Breslow intermediates.
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