A Highly Efficient Three-Component Coupling of Aldehyde, Alkyne, and Amines via C−H Activation Catalyzed by Gold in Water
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- 19 July 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (32), 9584-9585
- https://doi.org/10.1021/ja0359299
Abstract
A highly efficient three-component-coupling of aldehyde, alkyne, and amine (A3 Coupling) catalyzed by gold via C−H activation was developed in water. The reaction is general, and nearly quantitative yields of the corresponding propargylamines were obtained in most cases. Both aromatic and aliphatic aldehydes and amines can be used for the reaction. No additional cocatalyst or activator is required. A mechanistic rationale for the reaction has been proposed.Keywords
This publication has 14 references indexed in Scilit:
- The Barbier−Grignard-Type Carbonyl Alkylation Using Unactivated Alkyl Halides in WaterJournal of the American Chemical Society, 2003
- Quasi-Nature Catalysis: Developing C−C Bond Formations Catalyzed by Late Transition Metals in Air and WaterAccounts of Chemical Research, 2002
- The Discovery of Novel Reactivity in the Development of C−C Bond-Forming Reactions: In Situ Generation of Zinc Acetylides with ZnII/R3NAccounts of Chemical Research, 2000
- Silver catalyzed zinc Barbier reaction of benzylic halides in waterTetrahedron Letters, 1998
- Ruthenium-Catalyzed Reactions for Organic SynthesisChemical Reviews, 1998
- A New and Practical Synthesis of α-Amino Acids from Alkenyl Boronic AcidsJournal of the American Chemical Society, 1997
- Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applicationsTetrahedron, 1996
- The Atom Economy—A Search for Synthetic EfficiencyScience, 1991
- Crossed aldol type condensation reactions in aqueous mediaJournal of the Chemical Society, Chemical Communications, 1990
- Allylation of aldehydes and ketones in the presence of water by allylic bromides, metallic tin, and aluminumOrganometallics, 1983