Concepedia

Copper-Catalyzed Aerobic Oxidative Amidation of Terminal Alkynes:  Efficient Synthesis of Ynamides

Tetsuya Hamada, Xuan Ye, Shannon S. Stahl

Journal of the American Chemical Society · 2008 · 470 citations · 9 references

DOI

Concepts

Abstract

A copper-catalyzed method for the preparation of ynamides has been identified that proceeds via aerobic oxidative coupling of terminal alkynes with various nitrogen nucleophiles, including cyclic carbamates, amides and ureas, and N-alkyl-arylsulfonamides and indoles.

References

9

Acetylenic Coupling: A Powerful Tool in Molecular Construction

Peter Siemsen, R. C. Livingston, François Diederich · Angewandte Chemie International Edition · 2000 · 1.5K citations

, , +12

Palladium-Catalyzed Oxidation of Organic Chemicals with O <sub>2</sub>

Shannon S. Stahl · Science · 2005 · 501 citations

, , +16

Practical Synthesis of Amides from In Situ Generated Copper(<scp>I</scp>) Acetylides and Sulfonyl Azides

Michael P. Cassidy, Jessica Raushel, Valery V. Fokin · Angewandte Chemie International Edition · 2006 · 280 citations

, , +7

A Copper-Catalyzed C−N Bond Formation Involving sp-Hybridized Carbons. A Direct Entry to Chiral Ynamides via N-Alkynylation of Amides

Michael O. Frederick, Jason A. Mulder, Richard P. Hsung et al. · Journal of the American Chemical Society · 2003 · 226 citations

, , +7

Copper-Mediated N-Alkynylation of Carbamates, Ureas, and Sulfonamides. A General Method for the Synthesis of Ynamides

Joshua R. Dunetz, Rick Danheiser · Organic Letters · 2003 · 186 citations · Full text

, , +5