Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides

Synthesis of stable triazole anion equivalents

Brady T. Worrell, Shelby P. Ellery, Valery V. Fokin

Research output: Contribution to journalArticle

46 Citations (Scopus)

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 languageEnglish
Pages (from-to)13037-13041
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number49
DOIs
Publication statusPublished - 2 Dec 2013
Externally publishedYes

Fingerprint

Bismuth
Triazoles
Azides
Cycloaddition
Anions
Copper
Negative ions
Functional groups
Catalysts

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 journalArticle

@article{9ee44636c6b1432893c06436fd3da2b2,
title = "Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides: Synthesis of stable triazole anion equivalents",
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.",
keywords = "bismuth, click chemistry, copper, cycloaddition, heterocycles",
author = "Worrell, {Brady T.} and Ellery, {Shelby P.} and Fokin, {Valery V.}",
year = "2013",
month = "12",
day = "2",
doi = "10.1002/anie.201306192",
language = "English",
volume = "52",
pages = "13037--13041",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "49",

}

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

VL - 52

SP - 13037

EP - 13041

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 49

ER -