Bi(OTf)3 Enabled C‐F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane. Issue 8 (19th June 2018)

• Record Type: Journal Article
• Authors: Betterley, Nolan M.; Kerdphon, Sutthichat; Chaturonrutsamee, Suppisak; Kongsriprapan, Sopanat; Surawatanawong, Panida; Soorukram, Darunee; Pohmakotr, Manat; Andersson, Pher G.; Reutrakul, Vichai; Kuhakarn, Chutima
• Is Part Of: Asian journal of organic chemistry. Volume 7:Issue 8(2018)
• Page Start: 1642
• Page End: 1647
• Publication Date: 2018-06-19
• Subjects: aldehydes -- carbocations -- C−F activation -- electrophilic addition -- thionium cation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201800313
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Bismuth(III) trifluoromethanesulfonate [Bi(OTf)3 ] mediated mild electrophilic aromatic formylation utilizing difluoro(phenylsulfanyl)methane (PhSCF2 H) as a formylating agent in hexafluoro‐2‐propanol (HFIP) as a recyclable ionizing solvent has been developed. The active formylating species was generated via C−F bond cleavage and was characterized to be a bis(phenylsulfanyl)methyl cation by experimental and computational 1 H and 13 C NMR. Abstract : Form and function combine : Electrophilic aromatic formylation with difluoro(phenylsulfanyl)methane (PhSCF2 H) via C−F bond cleavage activated by bismuth(III) triflate and HFIP as a recyclable solvent is reported.