Publication:
Fluoride-Catalyzed Nucleophilic Addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to Isatins: Synthesis of 3-(1′,1′-Difluoroalkyl)-3-hydroxyindolin-2-ones

Issued Date

2018-01-23

Resource Type

Article

ISSN

10990690
1434193X

DOI

10.1002/ejoc.201701106

Other identifier(s)

2-s2.0-85040838611

Rights

Mahidol University

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SCOPUS

Bibliographic Citation

European Journal of Organic Chemistry. Vol.2018, No.3 (2018), 295-305

Suggested Citation

Sirisuk Keereewan, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Fluoride-Catalyzed Nucleophilic Addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to Isatins: Synthesis of 3-(1′,1′-Difluoroalkyl)-3-hydroxyindolin-2-ones. European Journal of Organic Chemistry. Vol.2018, No.3 (2018), 295-305. doi:10.1002/ejoc.201701106 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45511

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Title

Fluoride-Catalyzed Nucleophilic Addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to Isatins: Synthesis of 3-(1′,1′-Difluoroalkyl)-3-hydroxyindolin-2-ones

Author(s)

Sirisuk Keereewan
 Darunee Soorukram
 Chutima Kuhakarn
 Vichai Reutrakul
 Manat Pohmakotr

Other Contributor(s)

Mahidol University

Abstract

© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The synthesis of 3-(1′,1′-difluoroalkyl)-3-hydroxyindolin-2-ones by employing α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) as a gem-difluoromethylene building block is described. The reaction involves a fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to various isatin derivatives followed by the reductive cleavage of the phenylsulfanyl group to lead to 3-(difluoromethyl)-3-hydroxyindolin-2-ones in good yields. Under similar reduction conditions but in the presence of activated olefins, an intermolecular radical trapping reaction took place to yield 3-(1′,1′-difluoroalkyl)-3-hydroxyindolin-2-one derivatives.

Keyword(s)

Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/45511

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Scopus 2018