Molecules (Nov 2023)

Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents

  • Jiaqiong Sun,
  • Yunliang Guo,
  • Jiuli Xia,
  • Guangfan Zheng,
  • Qian Zhang

DOI
https://doi.org/10.3390/molecules28217420
Journal volume & issue
Vol. 28, no. 21
p. 7420

Abstract

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β-halogenated enol esters and ethers are versatile building blocks in organic synthesis, which has attracted increasing attention. In this study, we report the facile trans-oxyiodination and oxychlorination of alkynes, leading to the direct construction of versatile halogenated enol esters and ethers. This transformation features an easy operation, optimal atomic economy, a strong functional group tolerance, broad substrate scope, and excellent trans-selectivity. Employing highly electrophilic bifunctional N–X (halogen) reagents was the key to achieving broad reaction generality. To our knowledge, this transformation represents the first oxyhalogenation system employing N–X (halogen) reagents as both oxylation and halogenation sources.

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