Taking Advantage of the Ambivalent Reactivity of Ynamides in Gold Catalysis: A Rare Case of Alkyne Dimerization

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 det...

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Vydáno v:Angewandte Chemie International Edition Ročník 50; číslo 22; s. 5090 - 5094
Hlavní autoři: Kramer, Søren, Odabachian, Yann, Overgaard, Jacob, Rottländer, Mario, Gagosz, Fabien, Skrydstrup, Troels
Médium: Journal Article
Jazyk:angličtina
Vydáno: Weinheim WILEY-VCH Verlag 23.05.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Wiley-VCH Verlag
Vydání:International ed. in English
Témata:
Alkynes - chemistry
Amides - chemical synthesis
Amides - chemistry
Catalysis
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Cyclization
Dimerization
gold
Gold - chemistry
homogeneous catalysis
Organic chemistry
Physical Sciences
Science & Technology
synthetic methods
ynamides
C-H BOND
GOLD(I)-CATALYZED CYCLOISOMERIZATION
COMPLEXES
dimerization
gold
CYCLOADDITION
homogeneous catalysis
ynamides
STEREOSELECTIVE-SYNTHESIS
FUNCTIONALITIES
DERIVATIVES
synthetic methods
CYCLIZATION
TRANSFORMATIONS
ENYNES
ISSN:1433-7851, 1521-3773, 1521-3773
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Shrnutí: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).
Bibliografie:H. Lundbeck A/S
Carlsberg Foundation
ark:/67375/WNG-C2NGCRHL-1
ArticleID:ANIE201100327
OChem Graduate School
Ecole Polytechnique
Aarhus University
We are deeply appreciative of generous financial support from the Carlsberg Foundation, the Danish National Research Foundation, H. Lundbeck A/S, the OChem Graduate School, the Ecole Polytechnique and Aarhus University.
Danish National Research Foundation
istex:47EAF6E05DE1799DB308596A4336F2B61787222D
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201100327