“On-water” defluorinative cyclization of trifluoromethyl enones with phosphine oxides: synthesis of polysubstituted furans

Man Hang Feng, Shu Ji Gao, Xiao Ying Li, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The unique properties at the macroscopic phase boundary between water and insoluble reactants have the potential to enhance reaction rates and selectivity. In this work, a mild, transition-metal-free, and efficient defluorinative cyclization of readily available trifluoromethyl enones with phosphine oxides is developed in a pure water solution, involving a sequence of intermolecular defluorophosphorylation and intramolecular defluoroheterocyclization. A variety of polysubstituted furans featuring C1-fluorine, C2-trifluoromethyl, and C3-phosphoryl groups could be synthesized in good yields with excellent tolerance toward various functional groups. Moreover, these furans could be readily transformed into other structurally valuable furan derivatives. The utilization of water not only serves as an environmentally friendly solvent but also contributes to excellent reaction selectivity and selective C-F bond activation.

Original languageEnglish
Pages (from-to)3974-3981
Number of pages8
JournalOrganic Chemistry Frontiers
Volume11
Issue number14
DOIs
StatePublished - 29 May 2024

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