Concepedia

Bi(OTf)<sub>3</sub> Enabled C‐F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane

Nolan M. Betterley, Sutthichat Kerdphon, Suppisak Chaturonrutsamee, Sopanat Kongsriprapan, Panida Surawatanawong, Darunee Soorukram, Manat Pohmakotr, Pher G. Andersson, Vichai Reutrakul, Chutima Kuhakarn

Asian Journal of Organic Chemistry · 2018 · 14 citations · 41 references

DOI

Concepts

Abstract

Abstract Bismuth(III) trifluoromethanesulfonate [Bi(OTf) 3 ] mediated mild electrophilic aromatic formylation utilizing difluoro(phenylsulfanyl)methane (PhSCF 2 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.

References

41

Density-functional thermochemistry. III. The role of exact exchange

Axel D. Becke · The Journal of Chemical Physics · 1993 · 102.8K citations

, , +13

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density

Chengteh Lee, Weitao Yang, Robert G. Parr · Physical review. B, Condensed matter · 1988 · 100.1K citations

, , +17

Self-Consistent Molecular-Orbital Methods. IX. An Extended Gaussian-Type Basis for Molecular-Orbital Studies of Organic Molecules

R. Ditchfield, Warren J. Hehre, John A. Pople · The Journal of Chemical Physics · 1971 · 10.5K citations

, , +15

Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94

Thomas A. Halgren · Journal of Computational Chemistry · 1996 · 5.3K citations

, , +12

Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds using Quantum Chemical Calculations of NMR Shifts

Nicolás Grimblat, Marı́a M. Zanardi, Ariel M. Sarotti · The Journal of Organic Chemistry · 2015 · 1.3K citations · Full text

, , +8