Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

Autor(es)

Echemendia, Radell ; Montgomery, Carlee A. ; Cuzzucoli, Fabio ; Burtoloso, Antonio C. B. ; Murphy, Graham K.

• Tipo de documento: Artigo Científico
• Fonte: Beilstein Journal of Organic Chemistry; v. 20, p. 9-pg., 2024-12-04.

Resumo

A novel study on the hypervalent iodine-mediated polyfluoroalkylation of sulfoxonium ylides was developed. Sulfoxonium ylides, known for their versatility and stability, are promising substrates for numerous transformations in synthetic chemistry. This report demonstrates the successful derivatization of sulfoxonium ylides with trifluoroethyl or tetrafluoropropyl groups, and provides valuable insights into the scope and limitations of this approach. Nineteen examples have been prepared (45-92% yields), with structural diversity modified at two key sites on the sulfoxonium ylide reactants. Finally, DFT calculations provided insights about the mechanism of this transformation, which strongly suggest that an SN2 reaction is operative. (AU)

• Processo FAPESP: 23/02675-7 - Novas metodologias para formação de ligações C-C a partir de ilídeos sulfoxônios
• Beneficiário: Antonio Carlos Bender Burtoloso
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 19/12300-5 - Síntese de butenolídeos e butirolactamas a partir de reações entre ilídeos de enxofre e compostos diazocarbonílicos
• Beneficiário: Radell Echemendía Pérez
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado
• Processo FAPESP: 22/09140-9 - Transformação de ilídeos de sulfoxônio e compostos de iodo hipervalente
• Beneficiário: Radell Echemendía Pérez
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Pós-Doutorado