Efficient electrocatalytic addition reactions of allyl phenyl sulfone to electron deficient alkenes

The use of tetraalkylammonium salts as electrolytes has been found to allow the formation of electrogenerated bases of especially high reactivity. Such conditions allow allyl phenyl sulfone to undergo addition to a variety of electron deficient vinyl and propenyl compounds (sulfone, ketone, nitrile, and ester). The additions are catalyzed by electrogenerated bases derived from the reactant itself, rather than via an added pro-base. The nature of the substrate molecule is seen to affect which type of product is formed, leading to an interplay between addition to 1 mol of substrate or to 2 mol of substrate. Yields of 1:1 adducts range from 6 to 81%, while yields of 1:2 adducts range from 57 to 96%.