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Chemoselective Carbophilic Addition of α‐Diazoesters through Ligand‐Controlled Gold Catalysis
Author(s) -
Xi Yumeng,
Su Yijin,
Yu Zhaoyuan,
Dong Boliang,
McClain Edward J.,
Lan Yu,
Shi Xiaodong
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.201404946
Subject(s) - ligand (biochemistry) , cyclopropanation , catalysis , chemistry , nucleophile , carbocation , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , receptor , biochemistry
The chemoselective addition of arenes and 1,3‐diketones to α‐aryldiazoesters was achieved through ligand‐controlled gold catalysis. Unlike a dirhodium catalyst (which promotes C sp 3H insertion and cyclopropanation) and a copper catalyst (which catalyzes OH and NH insertions), the gold catalyst with an electron‐deficient phosphite as the ancillary ligand exclusively gave the carbophilic addition product, thus representing a new and efficient approach to form “carbophilic carbocations”, which selectively react with carbon nucleophiles.