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A Highly Efficient Three-Component Coupling of Aldehyde, Alkyne, and Amines via C-H Activation Catalyzed by Gold in Water

Chunmei Wei and Chao-Jun Li*

*Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, QC H3A 2K6 Canada, Email: cj.limcgill.ca

C. Wei, C.-J. Li, J. Am. Chem. Soc., 2003, 125, 9584-9585.

DOI: 10.1021/ja0359299


Abstract

A highly efficient gold-catalyzed three-component-coupling of aldehydes, alkynes, and amines in water was developed. Excellent yields of the corresponding propargylamines were obtained in most cases for both aromatic and aliphatic aldehydes and various amines.

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Details

The document discusses a highly efficient three-component coupling reaction of aldehyde, alkyne, and amines catalyzed by gold in water, developed by Chunmei Wei and Chao-Jun Li. This environmentally friendly method leverages C-H activation and uses less than 1 mol % of gold catalyst, with water as the only byproduct. The reaction is versatile, applicable to both aromatic and aliphatic aldehydes and amines, and achieves nearly quantitative yields without the need for cocatalysts or activators. Various gold salts, including AuCl, AuI, AuBr3, and AuCl3, were tested, with AuBr3 proving to be the most effective and cost-efficient. The reaction proceeds cleanly in water, while organic solvents result in lower conversions and more byproducts. The proposed mechanism involves the activation of the alkyne C-H bond by a Au(I) species, forming a gold acetylide intermediate that reacts with an immonium ion to produce propargylamine and regenerate the Au(I) catalyst. This method offers a simple, efficient, and sustainable approach to synthesizing propargylamines, with ongoing investigations into its scope, mechanism, stereoselectivity, and synthetic applications. The research was supported by NSF and the NSF-EPA joint program for a sustainable environment.


The First Silver-Catalyzed Three-Component Coupling of Aldehyde, Alkyne, and Amine

C. Wei, Z. Li, C.-J. Li, Org. Lett., 2003, 5, 4473-4475.


Key Words

propargylamines, multicomponent reactions, green chemistry


ID: J48-Y2003-1550