4.8 Article

Chelation-Assisted Interrupted Copper(I)-Catalyzed Azide-Alkyne-Azide Domino Reactions: Synthesis of Fully Substituted 5-Triazenyl-1,2,3-triazoles

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ORGANIC LETTERS
卷 23, 期 2, 页码 334-339

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03838

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资金

  1. MINECO [CTQ2014-57157-P, PPUENTE2020/007]
  2. FEDER program [CTQ2014-57157-P, PPUENTE2020/007]
  3. University of Almeria [CTQ2014-57157-P, PPUENTE2020/007]
  4. MECD

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Through a ligand-free domino copper(I)-catalyzed azide-alkyne-azide process, 1,4-(disubstituted)-5-triazenyl-1,2,3-triazoles were synthesized successfully, and the crucial role of Cu-chelation in the interception of the intermediate by the azide was revealed through DFT calculations and X-ray diffraction analysis.
We describe the synthesis of 1,4-(disubstituted)-5-triazenyl-1,2,3-triazoles through a ligand-free domino copper(I)-catalyzed azide-alkyne-azide process of chelating aryl azides bearing N-P=O, P=O, and SO3H groups at the ortho position with a wide variety of acetylenes. DFT calculations reveal that Cu-chelation is a crucial factor in the interception of the CuAAC intermediate by the azide. The crystal structure of the catalytic species has been determined by X-ray diffraction.

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