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Taking Advantage of the Ambivalent Reactivity of Ynamides in Gold Catalysis: A Rare Case of Alkyne Dimerization
Author(s) -
Kramer Søren,
Odabachian Yann,
Overgaard Jacob,
Rottländer Mario,
Gagosz Fabien,
Skrydstrup Troels
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.201100327
Subject(s) - alkyne , reactivity (psychology) , chemistry , catalysis , ambivalence , product (mathematics) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , mathematics , medicine , alternative medicine , pathology , psychology , social psychology , geometry
A gold mine of results : A series of ynamides have been dimerized in the presence of a gold(I) complex. This unprecedented transformation involves the formation of a key keteniminium intermediate that reacts to form a variety of cyclic and acyclic products. The substitution pattern of the ynamide determines which product is formed (see scheme; EWG=electron‐withdrawing group, Ts= p ‐toluenesulfonyl).