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Palladium‐Catalyzed Allylic Alkylation of Simple Ketones with Allylic Alcohols and Its Mechanistic Study
Author(s) -
Huo Xiaohong,
Yang Guoqiang,
Liu Delong,
Liu Yangang,
Gridnev Ilya D.,
Zhang Wanbin
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403410
Subject(s) - allylic rearrangement , chemistry , catalysis , palladium , tsuji–trost reaction , pyrrolidine , reagent , methanol , solvent , organic chemistry , alkylation , combinatorial chemistry
Allylic alcohols were directly used in Pd‐catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20 °C by the concerted action of a Pd catalyst, a pyrrolidine co‐catalyst, and a hydrogen‐bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π‐allylpalladium complex by lowering the activation barrier.