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Gold‐Catalyzed Intramolecular Redox Reaction of Sulfinyl Alkynes: Efficient Generation of α‐Oxo Gold Carbenoids and Application in Insertion into RCO Bonds
Author(s) -
Li Guotao,
Zhang Liming
Publication year - 2007
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.200701449
Subject(s) - intramolecular force , redox , chemistry , catalysis , sulfur , pinacol , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry
Golden touch : α‐Oxo Au carbenoids are efficiently generated by Au‐catalyzed intramolecular redox reactions of sulfinyl alkynes. Besides cyclization to form benzo‐fused sulfur‐containing rings, these intermediates can participate in subsequent pinacol‐type rearrangements, leading to a two‐step insertion of a latent vinylcarbonylmethylene group into aldehydes or ketones (see scheme for second step).