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 | |
| 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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