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Gold‐Catalyzed Cyclizations of cis ‐Enediynes: Insights into the Nature of Gold–Aryne Interactions
Author(s) -
Wang Youliang,
Yepremyan Akop,
Ghorai Subir,
Todd Robert,
Aue Donald H.,
Zhang Liming
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.201301057
Subject(s) - aryne , intramolecular force , chemistry , catalysis , nucleophile , combinatorial chemistry , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry
Golden aryne? Gold aryne complexes are inferred as transition states in dual gold‐catalyzed cyclizations of cis ‐enediynes (see scheme; DCE=1,2‐dichloroethane). They are better described as ortho ‐aurophenyl cations, which react with weak nucleophiles and undergo facile intramolecular insertions into C(sp 3 )H bonds. Indanes, fused heteroarenes, and phenol derivatives are readily prepared using this method.