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Hydrophenoxylation of Alkynes by Cooperative Gold Catalysis
Author(s) -
Oonishi Yoshihiro,
GómezSuárez Adrián,
Martin Anthony R.,
Nolan Steven P.
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.201304182
Subject(s) - carbene , lewis acids and bases , stereospecificity , chemistry , catalysis , aryl , base (topology) , brønsted–lowry acid–base theory , medicinal chemistry , reaction mechanism , combinatorial chemistry , organic chemistry , polymer chemistry , alkyl , mathematical analysis , mathematics
Double impact : The title method gives aryl vinyl ethers in high yields, short reaction times, Z ‐stereospecificity, and good regioselectivities. Insights into the reaction mechanism highlight the role of [{Au(NHC)} 2 (μ‐OH)][BF 4 ] (NHC=N‐heterocyclic carbene) as both a Lewis acid, [Au(NHC)][BF 4 ], and a Brønsted base, [Au(NHC)(OH)], thereby generating a synergistic effect between the two gold moieties.