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

Silvia Diez-Gonzalez; Andrea Correa; Luigi Cavallo; Steven Patrick Nolan

doi:10.1002/chem.200600961

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

Silvia Diez-Gonzalez, Andrea Correa, Luigi Cavallo, Steven Patrick Nolan

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

342 Citations (Scopus)

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 excellent 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 cycloaddition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.

Original language	English
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
Publication status	Published - 10 Oct 2006

Keywords

alkynes
azides
click chemistry
copper N-heterocyclic carbenes
COPPER(I)-CATALYZED 3-COMPONENT REACTION
HETEROCYCLIC CARBENE COMPLEXES
1,3-DIPOLAR CYCLOADDITION
TERMINAL ALKYNES
CLICK-CHEMISTRY
1,4-DISUBSTITUTED 1,2,3-TRIAZOLES
CATALYZED CYCLOADDITION
TRIMETHYLSILYL AZIDE
SOLID-PHASE
WATER

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10.1002/chem.200600961

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title = "(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes",

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 excellent 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 cycloaddition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.",

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author = "Silvia Diez-Gonzalez and Andrea Correa and Luigi Cavallo and Nolan, {Steven Patrick}",

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doi = "10.1002/chem.200600961",

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T1 - (NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes

AU - Diez-Gonzalez, Silvia

AU - Correa, Andrea

AU - Cavallo, Luigi

AU - Nolan, Steven Patrick

PY - 2006/10/10

Y1 - 2006/10/10

N2 - 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 excellent 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 cycloaddition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.

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 excellent 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 cycloaddition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.

KW - alkynes

KW - azides

KW - click chemistry

KW - copper N-heterocyclic carbenes

KW - COPPER(I)-CATALYZED 3-COMPONENT REACTION

KW - HETEROCYCLIC CARBENE COMPLEXES

KW - 1,3-DIPOLAR CYCLOADDITION

KW - TERMINAL ALKYNES

KW - CLICK-CHEMISTRY

KW - 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES

KW - CATALYZED CYCLOADDITION

KW - TRIMETHYLSILYL AZIDE

KW - SOLID-PHASE

KW - WATER

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U2 - 10.1002/chem.200600961

DO - 10.1002/chem.200600961

M3 - Article

SN - 0947-6539

VL - 12

SP - 7558

EP - 7564

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 29

ER -

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

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Keywords

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