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

(2006) CHEMISTRY-A EUROPEAN JOURNAL. 12(29). p.7558-7564
Author
Organization
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.
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

Citation

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MLA
Diez-Gonzalez, Silvia, et al. “(NHC)Copper(I)-Catalyzed [3+2] Cycloaddition of Azides and Mono- or Disubstituted Alkynes.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 12, no. 29, 2006, pp. 7558–64.
APA
Diez-Gonzalez, S., Correa, A., Cavallo, L., & Nolan, S. (2006). (NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes. CHEMISTRY-A EUROPEAN JOURNAL, 12(29), 7558–7564.
Chicago author-date
Diez-Gonzalez, Silvia, Andrea Correa, Luigi Cavallo, and Steven Nolan. 2006. “(NHC)Copper(I)-Catalyzed [3+2] Cycloaddition of Azides and Mono- or Disubstituted Alkynes.” CHEMISTRY-A EUROPEAN JOURNAL 12 (29): 7558–64.
Chicago author-date (all authors)
Diez-Gonzalez, Silvia, Andrea Correa, Luigi Cavallo, and Steven Nolan. 2006. “(NHC)Copper(I)-Catalyzed [3+2] Cycloaddition of Azides and Mono- or Disubstituted Alkynes.” CHEMISTRY-A EUROPEAN JOURNAL 12 (29): 7558–7564.
Vancouver
1.
Diez-Gonzalez S, Correa A, Cavallo L, Nolan S. (NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes. CHEMISTRY-A EUROPEAN JOURNAL. 2006;12(29):7558–64.
IEEE
[1]
S. Diez-Gonzalez, A. Correa, L. Cavallo, and S. Nolan, “(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 12, no. 29, pp. 7558–7564, 2006.
@article{8169898,
  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.},
  author       = {Diez-Gonzalez, Silvia and Correa, Andrea and Cavallo, Luigi and Nolan, Steven},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  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},
  language     = {eng},
  number       = {29},
  pages        = {7558--7564},
  title        = {(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes},
  url          = {http://dx.doi.org/10.1002/chem.200600961},
  volume       = {12},
  year         = {2006},
}

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