Silver-Catalyzed, Manganese-Mediated Allylation and Benzylation Reactions of Aldehydes and Ketones

摘要

Silver bromide catalyzes Barbier-type allylation of aldehydes and ketones using unactivated manganese powder. Aliphatic and aromatic aldehydes and ketones react, and aryl chlorides, nitriles, electron-donating and electron-withdrawing groups are tolerated. Benzylation using benzyl bromide also proceeds smoothly under these reaction conditions. Preliminary mechanistic studies are consistent with the formation a nucleophilic allylmetal intermediate. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)