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.
| Original language | English |
|---|---|
| Pages (from-to) | 13037-13041 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 52 |
| Issue number | 49 |
| DOIs | |
| Publication status | Published - 2 Dec 2013 |
| Externally published | Yes |
Keywords
- bismuth
- click chemistry
- copper
- cycloaddition
- heterocycles
ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
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Cite this
Worrell, B. T., Ellery, S. P., & Fokin, V. V. (2013). Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides: Synthesis of stable triazole anion equivalents. Angewandte Chemie - International Edition, 52(49), 13037-13041. https://doi.org/10.1002/anie.201306192