Synthesis of gem-Difluorinated Keto-Sulfoxides from Sulfoxonium Ylides.

Hayashi, Marcio; Burtoloso, Antonio C B

Hayashi, Marcio; Burtoloso, Antonio C B.

Afiliación

Hayashi M; Department of Physical Chemistry, São Carlos Institute of Chemistry, University of São Paulo CEP, SP-13563-120, São Carlos, Brazil.
Burtoloso ACB; Department of Physical Chemistry, São Carlos Institute of Chemistry, University of São Paulo CEP, SP-13563-120, São Carlos, Brazil.

Chemistry ; 30(21): e202400108, 2024 Apr 11.

Article en En | MEDLINE | ID: mdl-38318729

ABSTRACT

ABSTRACT

Organic molecules containing fluorine and sulfur atoms represent a large percentage of approved pharmaceuticals. Those with combination of both S and F atoms in their structure such as Xtandi, approved in 2012 for prostate cancer, indicates the importance of synthetic methods that accommodates both atoms in an organic moiety. In this study, a novel aspect of sulfoxonium ylide reactivity was explored, unveiling a streamlined and mild synthesis method for gem-difluorinated keto-sulfoxides. Our protocol offers a direct and practical approach to prepare these compounds in 14-80 % chemical yields, that were represented by 21 examples. NMR studies and Hammett correlations gave strong evidence about the mechanism of this transformation.

Palabras clave

Fluorinated Compounds; Selectfluor; Sulfoxide; Sulfoxonium Ylides; gem-difluoroalkyl

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Tipo de estudio: Guideline Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Alemania

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