Publication: Nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl compounds with PhSCF<inf>2</inf>H in the presence of a phosphazene as a base
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Issued Date
2014-01-01
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ISSN
10990690
1434193X
1434193X
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2-s2.0-84903376187
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Mahidol University
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SCOPUS
Bibliographic Citation
European Journal of Organic Chemistry. Vol.2014, No.19 (2014), 4162-4169
Suggested Citation
Teerachai Punirun, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl compounds with PhSCF<inf>2</inf>H in the presence of a phosphazene as a base. European Journal of Organic Chemistry. Vol.2014, No.19 (2014), 4162-4169. doi:10.1002/ejoc.201402162 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/33638
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Title
Nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl compounds with PhSCF<inf>2</inf>H in the presence of a phosphazene as a base
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Abstract
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.