Decarboxylative Anti-Michael Addition to Olefins Mediated by Photoredox Catalysis

Decarboxylative coupling of carboxylic acids with activated olefins has been accomplished using visible light photoredox catalysis. The strategic placement of a radical stabilizing aromatic group at the beta-position of the olefin component biases the regioselectivity of the addition, allowing reliable, facile access to anti-Michael-type products from readily available precursors. The scope of this methodology was demonstrated with a range of carboxylic acids and appropriately substituted olefins and was applied toward a two-step synthesis of the antiarrhythmic agent encainide.