Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

@article{Himo2005CopperIcatalyzedSO,
  title={Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.},
  author={F. Himo and T. Lovell and Robert Hilgraf and V. Rostovtsev and Louis Noodleman and K. Sharpless and V. Fokin},
  journal={Journal of the American Chemical Society},
  year={2005},
  volume={127 1},
  pages={
          210-6
        }
}
Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles. 
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