ChemistryOpen (Oct 2019)

Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides

  • Dr. Jinyang Chen,
  • Lan Mei,
  • Haiying Wang,
  • Li Hu,
  • Xiaorui Sun,
  • Dr. Jianwei Shi,
  • Dr. Qiang Li

DOI
https://doi.org/10.1002/open.201900246
Journal volume & issue
Vol. 8, no. 10
pp. 1230 – 1234

Abstract

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Abstract An efficient protocol for the synthesis of β‐hydroxy(alkoxy)selenides was developed through the electrochemical iodide‐catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides under mild reaction conditions. Mechanistic studies showed that the cation I+ is involved during the whole process, and accelerates the formation of seleniranium ion via substitution and addition reaction with dialkyl(aryl)diselenides and styrene derivatives. The corresponding products are formed in good to excellent yields. This electrochemical oxyselenation provides an efficient strategy for difunctionalization of alkenes.

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