(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and Mono- Or disubstituted alkynes

Silvia Díez-González; Andrea Correa; Luigi Cavallo; Steven P. Nolan

doi:10.1002/chem.200600961

(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and Mono- Or disubstituted alkynes

Silvia Díez-González, Andrea Correa, Luigi Cavallo, Steven P. Nolan^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

346 Scopus citations

Abstract

A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high reaction rates and excel lent yields were obtained in all cases. This catalytic system fulfils the requirements of "click chemistry" with its mild and convenient conditions, nota bly in water or solvent free reactions and simple isolation with no purification step. Furthermore, for the first time, an internal alkyne was successfully used in this copper-catalyzed cyclo-addition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic path-way for disubstituted alkynes.

Original language	English (US)
Pages (from-to)	7558-7564
Number of pages	7
Journal	Chemistry - A European Journal
Volume	12
Issue number	29
DOIs	https://doi.org/10.1002/chem.200600961
State	Published - Oct 10 2006
Externally published	Yes

Keywords

Alkynes
Azides
Click chemistry
Copper
N-heterocyclic carbenes

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

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10.1002/chem.200600961

Cite this

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abstract = "A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high reaction rates and excel lent yields were obtained in all cases. This catalytic system fulfils the requirements of {"}click chemistry{"} with its mild and convenient conditions, nota bly in water or solvent free reactions and simple isolation with no purification step. Furthermore, for the first time, an internal alkyne was successfully used in this copper-catalyzed cyclo-addition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic path-way for disubstituted alkynes.",

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AU - Díez-González, Silvia

AU - Correa, Andrea

AU - Cavallo, Luigi

AU - Nolan, Steven P.

PY - 2006/10/10

Y1 - 2006/10/10

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AB - A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high reaction rates and excel lent yields were obtained in all cases. This catalytic system fulfils the requirements of "click chemistry" with its mild and convenient conditions, nota bly in water or solvent free reactions and simple isolation with no purification step. Furthermore, for the first time, an internal alkyne was successfully used in this copper-catalyzed cyclo-addition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic path-way for disubstituted alkynes.

KW - Alkynes

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KW - Click chemistry

KW - Copper

KW - N-heterocyclic carbenes

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(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and Mono- Or disubstituted alkynes

Abstract

Keywords

ASJC Scopus subject areas

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