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Stereoselective Synthesis of Monofluoroalkenylphosphine Oxides via Photoinduced Decarboxylative Coupling of α-Fluoroacrylic Acids with P(O)H Compounds.

Xiao-Yu LuHong-Ye PanRui HuangKang YangXiang ZhangZi-Zhen WangQian-Qian TaoGui-Xian YangXiao-Juan WangHai-Pin Zhou
Published in: Organic letters (2023)
Herein, a practical and efficient method for synthesizing monofluoroalkenyl phosphine oxides via photoinduced decarboxylative/dehydrogenative coupling of α-fluoroacrylic acids with phosphine oxides and phosphonates has been developed. Various α-fluoroacrylic acids and P(O)H compounds containing relevant functional groups, including tetrafluorobenzene and pentafluorobenzene, were converted into corresponding products with excellent E -stereoselectivity in satisfactory yields. This method can be extended to achieve the synthesis of monofluoroalkenyl silanes under similar conditions.
Keyphrases
  • electron transfer
  • room temperature
  • visible light
  • ionic liquid