Publication:
Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o-Alkynylaryl Weinreb Amides

Issued Date

2017-12-15

Resource Type

Article

ISSN

10990690
1434193X

DOI

10.1002/ejoc.201701322

Other identifier(s)

2-s2.0-85038082745

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

European Journal of Organic Chemistry. Vol.2017, No.46 (2017), 6840-6850

Suggested Citation

Jongkonporn Phetcharawetch, Nolan M. Betterley, Darunee Soorukram, Manat Pohmakotr, Vichai Reutrakul, Chutima Kuhakarn Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o-Alkynylaryl Weinreb Amides. European Journal of Organic Chemistry. Vol.2017, No.46 (2017), 6840-6850. doi:10.1002/ejoc.201701322 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/42163

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Title

Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o-Alkynylaryl Weinreb Amides

Author(s)

Jongkonporn Phetcharawetch
 Nolan M. Betterley
 Darunee Soorukram
 Manat Pohmakotr
 Vichai Reutrakul
 Chutima Kuhakarn

Other Contributor(s)

Mahidol University

Abstract

© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim [Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride-induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were converted into difluoromethyl ketones through selective reductive cleavage of the phenylsulfanyl group. The reaction of o-alkynyl Weinreb amides derived from benzoic acid derivatives resulted in the formation of cyclized products through a 5-exo-dig cyclization.

Keyword(s)

Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/42163

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Scopus 2016-2017