4.5 Article

Bi(OTf)3 Enabled C-F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue 8, Pages 1642-1647

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201800313

Keywords

aldehydes; carbocations; C-F activation; electrophilic addition; thionium cation

Funding

  1. Center of Excellence for Innovation in Chemistry (PERCH-CIC)
  2. Office of the Higher Education Commission
  3. Thailand Research Fund [IRN58W0005, BRG6180005]
  4. Swedish Research Council (VR)
  5. Mahidol University under the National Research Universities Program of Thailand

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Bismuth(III) trifluoromethanesulfonate [Bi(OTf)(3)] mediated mild electrophilic aromatic formylation utilizing difluoro(phenylsulfanyl)methane (PhSCF2H) 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 H-1 and C-13 NMR.

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