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

Jia‐Yi Shou, Feng‐Ling Qing

2022Angewandte Chemie International Edition57 citationsDOI

Abstract

Abstract We report herein the three‐component radical addition reaction of SF 5 Cl, alkene and diazo compounds for the selective formation of α‐alkyl‐α‐SF 5 carbonyl compounds. The three‐component addition reaction proceeded through the first reaction of SF 5 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 5 carbonyl compounds were successfully prepared when allyl trimethylsilanes were used as the alkene substrates. Furthermore, the three‐component adducts formed from SF 5 Cl, α‐diazoacetophenones and vinyl acetates were converted into pentafluorosulfanylfurans. This transformation provided a practical and efficeint method for the synthesis of pentafluorosulfanylfurans.

Topics & Concepts

AlkeneChemistryDiazoAdductOrganic chemistryAlkylMedicinal chemistryCatalysisFluorine in Organic ChemistryCyclopropane Reaction MechanismsInorganic Fluorides and Related Compounds