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Copper(I)‐Catalyzed Cycloaddition of Bismuth(III) Acetylides with Organic Azides: Synthesis of Stable Triazole Anion Equivalents
Author(s) -
Worrell Brady T.,
Ellery Shelby P.,
Fokin Valery V.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306192
Subject(s) - bismuth , cycloaddition , copper , catalysis , chemistry , triazole , ion , combinatorial chemistry , organic chemistry , polymer chemistry , inorganic chemistry
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.