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A Method for Palladium‐Catalyzed Cross‐Couplings of Simple Alkyl Chlorides: Suzuki Reactions Catalyzed by [Pd 2 (dba) 3 ]/PCy 3
Author(s) -
Kirchhoff Jan H.,
Dai Chaoyang,
Fu Gregory C.
Publication year - 2002
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 - 10.1002/1521-3773(20020603)41:11<1945::aid-anie1945>3.0.co;2-7
Subject(s) - alkyl , chemistry , reactivity (psychology) , palladium , catalysis , ligand (biochemistry) , nonane , coupling reaction , coupling (piping) , medicinal chemistry , stereochemistry , organic chemistry , medicine , biochemistry , alternative medicine , receptor , mechanical engineering , engineering , pathology
The window of reactivity is relatively narrow in the first Suzuki cross‐coupling of alkyl chlorides with alkyl 9‐borabicyclo[3.3.1]nonane (9‐BBN) derivatives catalyzed by [Pd 2 (dba) 3 ] [Eq. (1); dba=( E , E )‐dibenzylideneacetone]: whereas good yields are obtained with the ligand tricyclohexylphosphane for ligands that are appreciably larger or smaller, essentially no coupling is observed. As the conditions are compatible with a variety of functional groups, this method introduces a new class of substrates into the family of potential partners in palladium‐catalyzed cross‐coupling reactions.