Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps

Stanislav V. Lozovskiy, Aleksander V. Vasilyev

Research outputpeer-review

Abstract

A two-step catalyst-free procedure for the construction of 3-perfluoroalkyl-2-(phosphoryl)methyl furans from commercially available 1-perfluoroalkyl 1,3-diketones is reported. Propargylic alcohols, prepared by direct alkynylation of the diketones, react with PCl3 via [2,3]-sigmatropic rearrangement – enolate cyclization sequence, leading to multifunctional furans. The reaction mechanism is supported by DFT study. In addition, the bioactivity modifying effect of phosphoryl group on 3-perfluoroalkyl furans is depicted. (Figure presented.).

Original languageEnglish
Pages (from-to)3121-3125
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number15
DOIs
Publication statusPublished - 4 Aug 2020

Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps'. Together they form a unique fingerprint.

Cite this