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Letter

Phosphine-Triggered Complete Chemo-Switch: From Efficient Aldehyde−Alkyne−Amine Coupling to Efficient Aldehyde−Alkyne Coupling in Water

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Xiaoquan Yao and Chao-Jun Li*

Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada

Org. Lett., 2005, 7 (20), pp 4395–4398

DOI: 10.1021/ol051575+

Publication Date (Web): August 30, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, cj.li@mcgill.ca

Abstract

A phosphine ligand served as a remarkable chemo-switch for the silver-catalyzed reaction of alkynes with aldehydes in the presence of amines in water. Exclusive aldehyde−alkyne−amine coupling product was observed in the absence of phosphine, whereas in the presence of a phosphine ligand, exclusive aldehyde−alkyne coupling product was obtained.

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Published In Issue September 29, 2005
Received July 5, 2005

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Letter

Phosphine-Triggered Complete Chemo-Switch: From Efficient Aldehyde−Alkyne−Amine Coupling to Efficient Aldehyde−Alkyne Coupling in Water

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

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

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

A New Entry in Catalytic Alkynylation of Aldehydes and Ketones: Dual Activation of Soft Nucleophiles and Hard Electrophiles by an Indium(III) Catalyst

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