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.

Original language	English
Pages (from-to)	13037-13041
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	49
DOIs	https://doi.org/10.1002/anie.201306192
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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10.1002/anie.201306192

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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 = dec,

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

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U2 - 10.1002/anie.201306192

DO - 10.1002/anie.201306192

M3 - Article

C2 - 24130150

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VL - 52

SP - 13037

EP - 13041

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 49