Three-Component Reaction of Pentafluorosulfanyl Chloride, Alkenes and Diazo Compounds and Synthesis of Pentafluorosulfanylfurans.

Angew Chem Int Ed Engl

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.

Published: September 2022

AI Article Synopsis

  • The study describes a three-component reaction combining sulfur pentachloride (SF Cl), alkenes, and diazo compounds for creating α-alkyl-α-SF carbonyl compounds.
  • It involves a two-step process where SF radicals first react with diazo compounds, leading to carbon radicals that then add to alkenes.
  • The method efficiently produces useful chemical compounds, including pentafluorosulfanylfurans, demonstrating its practical application in synthetic chemistry.

Article Abstract

We report herein the three-component radical addition reaction of SF Cl, alkene and diazo compounds for the selective formation of α-alkyl-α-SF carbonyl compounds. The three-component addition reaction proceeded through the first reaction of SF radical with the diazo compound followed by the addition of the in situ generated carbon radical to alkene. The synthetic useful α-allyl-α-SF carbonyl compounds were successfully prepared when allyl trimethylsilanes were used as the alkene substrates. Furthermore, the three-component adducts formed from SF Cl, α-diazoacetophenones and vinyl acetates were converted into pentafluorosulfanylfurans. This transformation provided a practical and efficeint method for the synthesis of pentafluorosulfanylfurans.

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http://dx.doi.org/10.1002/anie.202208860DOI Listing

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