Electrochemical Synthesis of Spiro[4.5]trienones through Radical-Initiated Dearomative Spirocyclization

Jiawei Hua, Zheng Fang, Mixue Bian, Tao Ma, Man Yang, Jia Xu, Cheng Kou Liu, Wei He, Ning Zhu, Zhao Yang, Kai Guo

Research output: Contribution to journalArticlepeer-review

85 Scopus citations

Abstract

A novel and green route has been developed for the electrochemical synthesis of spiro[4.5]trienones through radical-initiated dearomative spirocyclization of alkynes with diselenides. This metal-free and oxidant-free electrosynthesis reaction was performed in an undivided cell under mild conditions. A variety of selenation spiro[4.5]trienones products were prepared in moderate-to-good yields, showing a broad scope and functional group tolerance. Moreover, the developed continuous-flow system combined with electrosynthesis possesses the potential to achieve scaled-up reactions, overcoming the low efficiency of conventional electrochemical scaled-up reactions.

Original languageEnglish
Pages (from-to)2053-2059
Number of pages7
JournalChemSusChem
Volume13
Issue number8
DOIs
StatePublished - 21 Apr 2020

Keywords

  • dearomative spirocyclization
  • electrochemical synthesis
  • metal-free
  • oxidant-free
  • spiro[4.5]trienones

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