Room-Temperature Organocatalytic Cycloaddition of Azides with beta-Keto Sulfones: Toward Sulfonyl-1,2,3-triazoles

Autor(es)

Saraiva, Maiara T. ^[1] ; Costa, Gabriel P. ^[1] ; Seus, Natalia ^[1] ; Schumacher, Ricardo F. ^[1] ; Perin, Gelson ^[1] ; Paixao, Marcio W. ^[2] ; Luque, Rafael ^[3] ; Alves, Diego ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Pelotas UPPel, LASOL CCQFA, BR-96010900 Pelotas, RS - Brazil

^[2] Univ Fed Sao Carlos, Lab Sintese Prod Nat, BR-17012901 Sao Carlos, SP - Brazil

^[3] Univ Cordoba, Dept Quim Organ, Cordoba 5016 - Spain

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 17, n. 24, p. 6206-6209, DEC 18 2015.
• Citações Web of Science: 32

Resumo

Organocatalytic enamine-azide {[}3 + 2] cycloadditions between beta-keto sulfones and aryl azides can be performed at room temperature in good to excellent yields of products in the presence of catalytic amounts of pyrrolidine (5 mol %). The proposed organocatalytic methodology was found to be applicable to beta-keto arylsulfones containing a range of substituents. A wide variety of aryl azides also work. Basically, this constitutes a remarkably efficient protocol for the synthesis of novel 1,2,3-triazole compounds. (AU)

• Processo FAPESP: 15/17141-1 - Desenvolvimento e Estudos Mecanísticos de Novas Metodologias Sintéticas para Síntese de Compostos Bioativos
• Beneficiário: Ricardo Samuel Schwab
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia