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Silver‐Catalyzed, Manganese‐Mediated Allylation and Benzylation Reactions of Aldehydes and Ketones
Author(s) -
Barczak Nicholas T.,
Jarvo Elizabeth R.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800898
Subject(s) - chemistry , bromide , manganese , catalysis , aryl , organic chemistry , nucleophile , medicinal chemistry , benzyl bromide , alkyl
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)