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 |
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Keywords
- bismuth
- click chemistry
- copper
- cycloaddition
- heterocycles
ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
Cite this
Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides : Synthesis of stable triazole anion equivalents. / Worrell, Brady T.; Ellery, Shelby P.; Fokin, Valery V.
In: Angewandte Chemie - International Edition, Vol. 52, No. 49, 02.12.2013, p. 13037-13041.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides
T2 - Synthesis of stable triazole anion equivalents
AU - Worrell, Brady T.
AU - Ellery, Shelby P.
AU - Fokin, Valery V.
PY - 2013/12/2
Y1 - 2013/12/2
N2 - 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.
AB - 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.
KW - bismuth
KW - click chemistry
KW - copper
KW - cycloaddition
KW - heterocycles
UR - http://www.scopus.com/inward/record.url?scp=84888602200&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84888602200&partnerID=8YFLogxK
U2 - 10.1002/anie.201306192
DO - 10.1002/anie.201306192
M3 - Article
C2 - 24130150
AN - SCOPUS:84888602200
VL - 52
SP - 13037
EP - 13041
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 49
ER -