Oxidative Cross-Coupling of Cysteamine with Secondary Phosphine Chalcogenides: Aspects of Reaction Chemoselectivity

Cysteamine (2-aminoethanethiol) undergoes oxidative cross-coupling with secondary phosphine sulfides and phosphine selenides under mild conditions (room temperature, 2–5 h, CCl 4 /Et 3 N) to give products of monocoupling at the amino group (ethylchalcogenophosphinic amides with free SH functions) an...

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Bibliographic Details
Published in:Doklady. Chemistry 2020, Vol.490 (1), p.11-15
Main Authors: Khrapova, K. O., Gusarova, N. K., Telezhkin, A. A., Volkov, P. A., Ivanova, N. I., Larina, L. I., Apartsin, K. A., Kireeva, V. V., Trofimov, B. A.
Format: Article
Language:English
Subjects:
Amides
Carbon tetrachloride
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cross coupling
Cysteamine
Industrial Chemistry/Chemical Engineering
Phosphines
Room temperature
Selenides
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Summary:Cysteamine (2-aminoethanethiol) undergoes oxidative cross-coupling with secondary phosphine sulfides and phosphine selenides under mild conditions (room temperature, 2–5 h, CCl 4 /Et 3 N) to give products of monocoupling at the amino group (ethylchalcogenophosphinic amides with free SH functions) and dicoupling (l-chalcogenophosphorylamino-2-chalcogenothioethanes) in 72–85% total yield. Under similar conditions, stirring an equimolar mixture of bis(2-phenylethyl)phosphine sulfide (or selenide), 1-butylamine, and 1-butanethiol leads to the chemoselective formation of the corresponding chalcogenophosphinic amides in high yield.
ISSN:0012-5008
1608-3113
DOI:10.1134/S0012500820010048