Photoredox-Catalyzed Hydrocarboxymethylation of Alkenes

Direct introduction of a carboxyl group into molecules is one of the most useful methods for the preparation of carboxylic acids, which avoids the conversion of various preexisting functional groups and features good step- and atom-economy. However, the methods for the direct synthesis of two-carbon added carboxylic acids from the precursors remain rare. Herein, we first report a general and mild method for the direct synthesis of a range of aliphatic acids by photoredox-catalyzed hydrocarboxymethylation of alkenes with good toleration of various functional groups in which bromoacetic acid is utilized as an ideal two-carbon synthon. The synthetic utility of this hydrocarboxymethylation protocol is further demonstrated by the concise synthesis of two marketed drugs, sensipar and tirofiban, from commercially available starting materials. [GRAPHICS] .