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Copper(I)/Succinic Acid Cooperatively Catalyzed One-pot Synthesis of Organoselenium-propargylamines via A3-Coupling

Abstract

Selenium propargylamines were synthesized via an A3 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 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 coupling constant (J) values in 1H NMR spectra. The vinyl selenides were employed in Sonogashira cross-coupling reactions to produce corresponding enynes, with yields ranging from moderate to good.

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Publication details

The article was received on 29 Mar 2018, accepted on 08 May 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C8NJ01543K
Citation: New J. Chem., 2018, Accepted Manuscript
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    Copper(I)/Succinic Acid Cooperatively Catalyzed One-pot Synthesis of Organoselenium-propargylamines via A3-Coupling

    H. A. Stefani, I. M. Oliveira, D. C. Pimenta, J. Zukerman-Schpector and F. G. Manarin, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ01543K

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