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Characterization of Vinylgold Intermediates: Gold‐Mediated Cyclization of Acetylenic Amides
Author(s) -
Egorova Olga A.,
Seo Hyewon,
Kim Yonghwi,
Moon Dohyun,
Rhee Young Min,
Ahn Kyo Han
Publication year - 2011
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.201106132
Subject(s) - chemistry , acetonitrile , propargyl , substrate (aquarium) , reaction intermediate , reactive intermediate , aqueous medium , gold compounds , aqueous solution , organic chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , catalysis , oceanography , geology
Hidden nuggets of gold : Mono‐ and divinylgold complexes (see scheme), key intermediates in the gold‐mediated cyclization reaction of N ‐(propargyl)benzamides, are characterized by NMR and X‐ray diffraction analyses. The monovinylgold intermediates undergo proto‐deauration in acetonitrile by the substrate. In aqueous media, they produce oxidized products. The divinylgold species undergo reductive elimination to produce the corresponding dimerized products.