Copper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A(3)-coupling

Autor(es)

de Oliveira, Isadora M. ^[1] ; Pimenta, Daniel C. ^[2] ; Zukerman-Schpector, Julio ^[3] ; Stefani, Helio A. ^[4] ; Manarin, Flavia ^[5]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo, SP - Brazil

^[2] Inst Butantan, Lab Bioquim & Biofis, Sao Paulo, SP - Brazil

^[3] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP - Brazil

^[4] Univ Sao Paulo, Dept Farm, Fac Ciencias Farmaceut, Sao Paulo, SP - Brazil

^[5] Univ Estadual Oeste Parana, CECE, Toledo, PR - Brazil

• Tipo de documento: Artigo Científico
• Fonte: NEW JOURNAL OF CHEMISTRY; v. 42, n. 12, p. 10118-10123, JUN 21 2018.
• Citações Web of Science: 2

Resumo

Selenium propargylamines were synthesized via an A(3)-coupling approach using piperidine, p-methoxybenzaldehyde, and trimethylsilyl selenium-acetylene, catalyzed by copper(i) chloride and succinic acid as an additive, in good to excellent yields. This method is advantageous in that desilylation of the trimethylsilyl selenium-acetylene occurs in situ. The reaction time was monitored by FTIR studies and a probable mechanism is described. Scale-up was also performed in satisfactory yield. These selenium propargylamines could be hydrohalogenated to synthesize halovinyl selenides. The stereochemistry was determined by treatment with n-butyllithium and the coupling constant (J) values in H-1 NMR spectra. The vinyl selenides were employed in Sonogashira cross-coupling reactions to produce the corresponding enynes, with yields ranging from moderate to good. (AU)

• Processo FAPESP: 16/04289-3 - Síntese de derivados calcogenoaminoácidos e 4-calcogenoquinolinas via reações multicomponentes
• Beneficiário: Isadora Maria de Oliveira
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto