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Palladium-catalyzed conjugate allylation reactions of alpha,beta-unsaturated N-acylpyrroles.

Conjugate allylation reactions of alpha,beta-unsaturated N-acylpyrroles using allylboronic ester are catalyzed by a palladium complex that is ligated by a bidentate N-heterocyclic carbene. A variety of functional groups are tolerated, and substrates functionalized with electron-withdrawing groups react to afford the highest yields of products. Regioselectivity for 1,4-allylation over 1,2-allylation is demonstrated, and mechanistic experiments are consistent with formation of nucleophilic allylpalladium intermediates.