Copper(I)‐Catalyzed Cycloaddition of Bismuth(III) Acetylides with Organic Azides: Synthesis of Stable Triazole Anion Equivalents1. Issue 49 (15th October 2013)

• Record Type: Journal Article
• Authors: Worrell, Brady T.; Ellery, Shelby P.; Fokin, Valery V.
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 49(2013)
• Page Start: 13037
• Page End: 13041
• Publication Date: 2013-10-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201306192
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Fully loaded</bold>: 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.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t7b0579" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>