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: fokin
scripps.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
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
ID: J54-Y2010-2670
