Direct Synthesis of alpha-Fluoro-alpha-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach

Autor(es)

Day, David Philip ^[1] ; Mora Vargas, Jorge Andres ^[1] ; Bender Burtoloso, Antonio Carlos ^[1]

Afiliação do(s) autor(es)

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

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 86, n. 17, p. 12427-12435, SEP 3 2021.
• Citações Web of Science: 0

Resumo

The work reported herein showcases a new route to access alpha-fluoro-alpha-triazol-1-yl ketones from sulfoxonium ylides via aazido-alpha-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N-3(-), followed by a subsequent CuAAC reaction with arylacetylenes to install a 1,4-triazolo moiety. The approach allows for modification to both the sulfoxonium ylide and arylacetylene reactants. Fifteen examples have been reported, with yields ranging between 22% and 75%. (AU)

• Processo FAPESP: 20/07147-0 - Alfa-heterofuncionalização enantioseletiva de compostos carbonílicos empregando ilídeos sulfoxônios
• Beneficiário: Antonio Carlos Bender Burtoloso
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 19/05002-8 - Investigando Transformações Enantiosseletivas de Diazocetonas e Ilídeos Sulfoxônios.
• Beneficiário: David Philip Day
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado