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Highly Linear Selective Cobalt‐Catalyzed Addition of Aryl Imines to Styrenes: Reversing Intrinsic Regioselectivity by Ligand Elaboration
Author(s) -
Xu Wengang,
Yoshikai Naohiko
Publication year - 2014
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.201408028
Subject(s) - regioselectivity , chemistry , ligand (biochemistry) , lewis acids and bases , phosphine , imine , cobalt , catalysis , aryl , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , biochemistry , receptor
Highly linear selective, imine‐directed hydroarylation of styrene has been achieved with cobalt‐based catalytic systems featuring bis(2,4‐dimethoxyphenyl)(phenyl)phosphine and either 2‐methoxypyridine or DBU as a ligand and a Lewis base additive, respectively, thus affording a variety of 1,2‐diarylethanes (bibenzyls) in good yields under mild reaction conditions. The triarylphosphine controls the regioselectivity, while the Lewis base significantly accelerates the reaction. Ligand screening and deuterium‐labeling studies provide implications about the roles of the ligand and the Lewis base in the crucial CC reductive elimination step.