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Palladium‐Catalyzed Oxidative Arylalkylation of Activated Alkenes: Dual CH Bond Cleavage of an Arene and Acetonitrile
Author(s) -
Wu Tao,
Mu Xin,
Liu Guosheng
Publication year - 2011
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.201104575
Subject(s) - acetonitrile , aniline , chemistry , olefin fiber , palladium , bond cleavage , yield (engineering) , catalysis , combinatorial chemistry , medicinal chemistry , cleavage (geology) , photochemistry , organic chemistry , materials science , fracture (geology) , metallurgy , composite material
Not one but two : The title reaction proceeds through the dual CH bond cleavage of both aniline and acetonitrile (see scheme). The reaction affords a variety of cyano‐bearing indolinones in excellent yield. Mechanistic studies demonstrate that this reaction involves a fast arylation of the olefin and a rate‐determining CH activation of the acetonitrile.