Indium-Catalyzed Highly Efficient Three-Component Coupling of Aldehyde, Alkyne, and Amine via C−H Bond Activation

In this paper, indium(III) chloride was found to be a highly effective catalyst for the three-component coupling reactions of aldehydes, alkynes, and amines (A3-coupling) via C−H activation. The reactions could be applied to both aromatic and aliphatic aldehydes and alkynes. Nearly quantitative yiel...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-06, Vol.74 (11), p.4364-4367
Main Authors: Zhang, Yicheng, Li, Pinhua, Wang, Min, Wang, Lei
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Aliphatic compounds
Alkynes - chemistry
Amines - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Indium - chemistry
Kinetics and mechanisms
Organic chemistry
Organic Chemistry Phenomena
Preparations and properties
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:In this paper, indium(III) chloride was found to be a highly effective catalyst for the three-component coupling reactions of aldehydes, alkynes, and amines (A3-coupling) via C−H activation. The reactions could be applied to both aromatic and aliphatic aldehydes and alkynes. Nearly quantitative yields of the desired products were obtained in most cases. No cocatalyst or activator is required, and water is the only byproduct in the reactions. Furthermore, a tentative mechanism of the InCl3-catalyzed one-pot, three-component coupling of aldehyde, alkyne, and amine is proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900507v