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

Autor(es)

Dias, Rafael M. P. ^[1] ; Burtoloso, Antonio C. B. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 18, n. 12, p. 3034-3037, JUN 17 2016.
• Citações Web of Science: 29

Resumo

Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing beta-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. (AU)

• Processo FAPESP: 13/25504-1 - Desenvolvimento de novas metodologias para a-funcionalização assimétrica de compostos carbonílicos utilizando catalisadores quirais
• Beneficiário: Antonio Carlos Bender Burtoloso
• Linha de fomento: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/18009-4 - Planejamento, síntese e atividade tripanossomicida de inibidores covalentes reversíveis da enzima cruzaína
• Beneficiário: Carlos Alberto Montanari
• Linha de fomento: Auxílio à Pesquisa - Temático