Betterley NM1, Surawatanawong P, Prabpai S, Kongsaeree P, Kuhakarn C, Pohmakotr M, Reutrakul V.
Org Lett. 2013 Nov 15;15(22):5666-9. doi: 10.1021/ol402631t. Epub 2013 Nov 1.Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of α-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2(+)).