β-Ketophosphonate Formation via Aerobic Oxyphosphorylation of Alkynes or Alkynyl Carboxylic Acids with H-Phosphonates

Mingxin Zhou(Huaqiao University), Ming Chen(University of Science and Technology of China), Yao Zhou(Huaqiao University), Kai Yang(Huaqiao University), Ji‐Hu Su(University of Science and Technology of China), Jiangfeng Du(University of Science and Technology of China), Qiuling Song(Huaqiao University)
Organic Letters
March 25, 2015
Cited by 111

Abstract

A synergistic Cu/Fe-catalyzed aerobic oxyphosphorylation of alkynes or alkynyl carboxylic acids with H-phosphonate is disclosed. The useful β-ketophosphonate products were obtained in good yields under oxygen atmosphere in a novel way. This reaction exhibits a wide substrate scope, and the mechanistic experiments indicate that a radical mechanism forms both C-P and C═O bonds simultaneously. This mechanism contrasts existing aerobic difunctionalization of alkynes.


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