Copper(I)-Catalyzed Cycloaddition of Bismuth(III) Acetylides with Organic Azides: Synthesis of Stable Triazole Anion Equivalents†
Brady T. Worrell
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin
Search for more papers by this authorDr. Shelby P. Ellery
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin
Search for more papers by this authorCorresponding Author
Prof. Valery V. Fokin
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin===Search for more papers by this authorBrady T. Worrell
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin
Search for more papers by this authorDr. Shelby P. Ellery
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin
Search for more papers by this authorCorresponding Author
Prof. Valery V. Fokin
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin===Search for more papers by this authorThis work was supported by the National Institute of General Medical Sciences, National Institutes of Health (GM-087620). Prof. Jason Hein (U.C. Merced), Dr. David Sarlah, and Will Gutekunst are gratefully acknowledged for helpful scientific discussions.
Graphical Abstract
Fully loaded: Readily accessible and shelf-stable 1-bismuth(III) acetylides react rapidly and regiospecifically with organic azides in the presence of a copper(I) catalyst (see scheme). The reaction tolerates many functional groups and gives excellent yields of the previously unreported 5-bismuth triazolides. This uniquely reactive intermediate is functionalized under mild reaction conditions to give fully substituted 1,2,3-triazoles.
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