Difluorocarbene

Difluorocarbene

Interfacial Catalysis at Oil/Water Interfaces

Published in Alexander G. Vdlkdv, Interfacial Catalysis, 2002

It was shown that difluorocarbene can be generated in the PT-catalyzed system via halophilic reaction of tribromomethyl [78] or dibromomethyl [79] carbanions with dibromodifluoromethane. In this process, the short-lived bromodifluoromethyl carbanion and consequently diffuorocarbene are generated inside the organic phase; thus, the latter can react efficiently with alkenes to produce gem-difluorocyclopropane derivatives. This method is limited to highly nucleophilic alkenes, but because of its simplicity it can be recommended as a method of choice in these cases.

Recent trends in direct mono-, di-, and tri-fluoromethyl(thiol)ation of S-H bonds

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Journal Information

Published in Journal of Sulfur Chemistry, 2019

Akram Hosseinian, Yahya Jamal Sadeghi, Saeideh Ebrahimiasl, Aazam Monfared, Esmail Vessally

In 2009, Zhang, Wang, and Hu synthesized the first α-difluoromethyl sulfoximine compound [PhSO(NTs)CH2F] by Cu-catalyzed reaction of difluoromethyl phenyl sulfoxide [PhS(O)CF2H] with PhI = NTs in MeCN [50]. The prepared sulfoximine compound was successfully applied as an efficient difluoromethylation reagent for transferring the CF2H group to thiolates, derived from a facile deprotonation of thiols 10 with NaH, in DMF at 60°C. Various difluoromethyl sulfides 11 were successfully synthesized employing this strategy (Scheme 5). The protocol also successfully applied in the difluoromethylation of N- and C-nucleophiles. The mechanism of this transformation was proposed based on the deuterium-labeling experiments, determining that the reaction proceeds via a difluorocarbene intermediate (Scheme 6).

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Interfacial Catalysis at Oil/Water Interfaces

Recent trends in direct mono-, di-, and tri-fluoromethyl(thiol)ation of S-H bonds