Transition-metal-free defluorinative cyclization of perfluoroalkyl alkenyl iodides with C,N-dinucleophiles: Synthesis of (E)-perfluoroalkenyl pyrroles

Yu Lan Chen, Wen Jun Ji, Yuan Yuan Ren, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Functionalization of the C-F bond in perfluoroalkyl substances represents an emerging focus in organic chemistry. We report here a transition-metal-free intermolecular defluorinative cyclization of perfluoroalkyl alkenyl iodides with C,N-dinucleophiles. This method enables highly chemo-, regio-, and stereoselective 2-fold C (sp3)-F bond cleavage at two vicinal carbon centers in the perfluoroalkyl chain, resulting in the assembly of a five-membered N-heterocycle with a structurally privileged (E)-prefluoroalkenyl unit. The success of partial defluorination is mainly attributed to the pre-installed alkenyl functionality and iodide atom in perfluoroalkyl substances.

Original languageEnglish
JournalGreen Synthesis and Catalysis
DOIs
StateAccepted/In press - 2024

Keywords

  • C-F bond functionalization
  • Defluorinative cyclization
  • Heterocycles
  • Perfluoroalkyl alkene
  • PFASs
  • Pyrrole
  • Transition-metal-free conditions

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