Frontiers in Chemistry (Apr 2021)

One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

  • Fa-Jie Chen,
  • Fa-Jie Chen,
  • Zhenguo Hua,
  • Jianhui Chen,
  • Jiajia Chen,
  • Daesung Lee,
  • Yuanzhi Xia

DOI
https://doi.org/10.3389/fchem.2020.621545
Journal volume & issue
Vol. 8

Abstract

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Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

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