Nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl compounds with PhSCF<inf>2</inf>H in the presence of a phosphazene as a base

• Main Authors: Teerachai Punirun, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr
• Other Authors: Mahidol University
• Format: Article
• Published: 2018
• Subjects: Chemistry
• Online Access: https://repository.li.mahidol.ac.th/handle/123456789/33638

Direct nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl compounds has been achieved by use of difluoro(phenylsulfanyl)methane (PhSCF2H) and the phosphazene base P4-tBu in THF. Non-enolizable aldehydes and ketones are suitable substrates to undergo nucleophilic gem-difluoro(phenylsulfanyl)methylation, providing α-gem-difluoromethylated adducts in good yields. In addition, this methodology is also applicable with cyclic imides and acid anhydrides. Direct nucleophilic gem-difluoro(phenylsulfanyl)methylation of aromatic aldehydes and ketones, cyclic imides, and acid anhydrides with difluoro(phenylsulfanyl)methane (PhSCF2H) reagent was achieved in the presence of the phosphazene P4-tBu as a base. The corresponding adducts should be useful for further synthetic conversion into a variety of fluorinated compounds. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.