Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of ß-Keto Thioethers.

Dias, Rafael M P; Burtoloso, Antonio C B

Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of ß-Keto Thioethers.

Dias, Rafael M P; Burtoloso, Antonio C B.

Afiliação

Dias RM; Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970 São Carlos, SP, Brazil.
Burtoloso AC; Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970 São Carlos, SP, Brazil.

Org Lett ; 18(12): 3034-7, 2016 06 17.

Article em En | MEDLINE | ID: mdl-27258164

RESUMO

Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing ß-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room temperature. Additional experimental as well as kinetic isotopic effect studies give some insight into the mechanism of this reaction.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2016 Tipo de documento: Article País de afiliação: Brasil País de publicação: Estados Unidos

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