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0 202608013

DOI: https://doi.org/10.6023/cjoc202608013

ARTICLE

Electrochemical Oxidative Fluorination of Phosphine Oxides with Sulfur Hexafluoride

  • Yue Zhao ,
  • Shan Zhu ,
  • Fengxiang Ma ,
  • Tao Lin ,
  • Chen Hang ,
  • Jun Cao ,
  • Yumei Song
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  • aState Grid Anhui Electric Power Research Institute, Hefei, 230601

Received date: 2026-08-12

  Revised date: 2026-09-09

  Online published: 2026-09-22

Supported by

State Grid Anhui Electric Power Co., Ltd. Technology Project (No. B3120524000K).

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Abstract

Organophosphorus fluorides are valuable motifs in chemical biology, medicinal chemistry, and synthesis, yet their preparation commonly relies on costly or operationally demanding fluorinating reagents. Herein, we describe a constant-current electrochemical oxidative fluorination of phosphine oxides using sulfur hexafluoride (SF6) as the fluorine source. A range of diaryl and alkyl-substituted phosphine oxides is converted to the corresponding P(O)-F products in moderate to good isolated yields, reaching up to 72%. The transformation is proposed to combine cathodic single-electron reduction of SF6, which furnishes fluoride-containing reduced fragments, with anodic oxidation of the phosphine oxide. Fluoride capture of the resulting phosphinoyl radical cation, followed by proton-coupled electron transfer, furnishes the P(O)-F bond. This study provides an electrode-driven route to use a persistent fluorinated greenhouse gas as a fluorine feedstock for organophosphorus synthesis.

Key words： sulfur hexafluoride; electrochemistry; oxidative fluorination; phosphine oxides; phosphorus-fluorine bond

Cite this article

Yue Zhao , Shan Zhu , Fengxiang Ma , Tao Lin , Chen Hang , Jun Cao , Yumei Song . Electrochemical Oxidative Fluorination of Phosphine Oxides with Sulfur Hexafluoride[J]. Chinese Journal of Organic Chemistry, 0 : 202608013 . DOI: 10.6023/cjoc202608013

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