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Transition-Metal-Free Catalytic Synthesis of 1,5-Diaryl-1,2,3-triazoles

Sen W. Kwok, Joseph R. Fotsing, Rebecca J. Fraser, Valentin O. Rodionov and Valery V. Fokin*

*The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, Email: fokinscripps.edu

S. W. Kwok, J. R. Fotsing, R. J. Fraser, V. O. Rodinov, V. V. Fokin, Org. Lett., 2010, 12, 4217-4219.

DOI: 10.1021/ol101568d (free Supporting Information)


Abstract

1,5-Diarylsubstituted 1,2,3-triazoles are formed in high yield from aryl azides and terminal alkynes in DMSO in the presence of a catalytic amount of tetraalkylammonium hydroxide or t-BuOK for base-labile substrates. The reaction is experimentally simple, does not require a transition-metal catalyst, and is not sensitive to atmospheric oxygen and moisture.

see article for more examples


proposed mechanism



Ruthenium-Catalyzed Cycloaddition of Aryl Azides and Alkynes

L. K. Rasmussen, B. C. Boren, V. V. Fokin, Org. Lett., 2007, 9, 5337-5339.


Key Words

1,2,3-triazoles


ID: J54-Y2010-2670