NDLI: Copper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A3-coupling

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Copper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A3-coupling

Content Provider	Semantic Scholar
Author	Oliveira, Isadora Maria De Pimenta, Daniel Carvalho Zukerman-Schpector, Júlio Stefani, Hélio Alexandre Manarin, Flávia
Copyright Year	2018
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 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 1H NMR spectra. The vinyl selenides were employed in Sonogashira cross-coupling reactions to produce the corresponding enynes, with yields ranging from moderate to good.
Starting Page	10118
Ending Page	10123
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/C8NJ01543K
Volume Number	42
Alternate Webpage(s)	http://www.rsc.org/suppdata/c8/nj/c8nj01543k/c8nj01543k1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/C8NJ01543K
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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