Copper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A3-coupling
New J. Chem.
; 42(12): p. 10118-10123, 2018.
Artigo
em Inglês
| Sec. Est. Saúde SP, SESSP-IBPROD, Sec. Est. Saúde SP
| ID: but-ib15248
Biblioteca responsável:
BR78.1
Localização: BR78.1
ABSTRACT
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.
Texto completo:
Disponível
Coleções:
Bases de dados nacionais
/
Brasil
Base de dados:
Sec. Est. Saúde SP
/
SESSP-IBPROD
Idioma:
Inglês
Revista:
New J. Chem.
Ano de publicação:
2018
Tipo de documento:
Artigo