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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
de Oliveira, Isadora M. [1] ; Pimenta, Daniel C. [2] ; Zukerman-Schpector, Julio [3] ; Stefani, Helio A. [4] ; Manarin, Flavia [5]
Total Authors: 5
Affiliation:
[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
Total Affiliations: 5
Document type: Journal article
Source: NEW JOURNAL OF CHEMISTRY; v. 42, n. 12, p. 10118-10123, JUN 21 2018.
Web of Science Citations: 2
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. (AU)

FAPESP's process: 16/04289-3 - Synthesis of calcogeno amino acids derivatives and 4-calcogeno quinolines via multicomponent reactions
Grantee:Isadora Maria de Oliveira
Support Opportunities: Scholarships in Brazil - Doctorate (Direct)