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Weak Arene CH⋅⋅⋅O Hydrogen Bonding in Palladium‐Catalyzed Arylation and Vinylation of Lactones
Author(s) -
Huang Zhiyan,
Chen Zuliang,
Lim Li Hui,
Quang Gia Chuong Phan,
Hirao Hajime,
Zhou Jianrong Steve
Publication year - 2013
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.201300481
Subject(s) - palladium , stereocenter , catalysis , chemistry , hydrogen bond , hydrogen , medicinal chemistry , polymer chemistry , stereochemistry , organic chemistry , molecule , enantioselective synthesis
Weak force in action : In the title reaction, the palladium catalyst (see figure, left) uses weak CH⋅⋅⋅O hydrogen bonding to control the absolute configuration of the new stereocenter. A similar palladium catalyst (right) used conventional NH⋅⋅⋅O hydrogen bonding to guide stereoselection.