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Palladium‐Catalyzed Alkylation of 1,4‐Dienes by CH Activation
Author(s) -
Trost Barry M.,
Hansmann Max M.,
Thaisrivongs David A.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201200601
Subject(s) - nucleophile , alkylation , tsuji–trost reaction , catalysis , chemistry , palladium , diene , medicinal chemistry , sulfoxide , dimethyl sulfoxide , organic chemistry , natural rubber
Activated : The title reaction proceeds with a broad range of nucleophiles and variously substituted 1,4‐dienes under mild conditions, and provides direct access to the corresponding 1,3‐diene‐containing products with high regio‐ and stereocontrol (see scheme; 2,6‐DMBQ=2,6‐dimethylbenzoquinone, EWG=electron‐withdrawing group). This is the first catalytic allylic CH alkylation that proceeds in the absence of sulfoxide ligands.