One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system

Phenanthridine readily undergoes one-pot N -acylvinylation/ C -phosphorylation in the terminal acetylenic ketone—secondary phosphine oxide system at room temperature (acetonitrile, 48–72 h) in the absence of a catalyst to stereoselectively form ( E )- N -acylvinyl-6-diorganylphosphoryl-5,6-dihydroph...

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Bibliographic Details
Published in:Russian chemical bulletin 2023-04, Vol.72 (4), p.955-959
Main Authors: Volkov, P. A., Khrapova, K. O., Telezhkin, A. A., Albanov, A. I., Trofimov, B. A.
Format: Article
Language:English
Subjects:
Acetonitrile
Adducts
Catalysts
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Ketones
Organic Chemistry
Phosphine oxide
Phosphorylation
Room temperature
Stereoselectivity
Sulfides
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Summary:Phenanthridine readily undergoes one-pot N -acylvinylation/ C -phosphorylation in the terminal acetylenic ketone—secondary phosphine oxide system at room temperature (acetonitrile, 48–72 h) in the absence of a catalyst to stereoselectively form ( E )- N -acylvinyl-6-diorganylphosphoryl-5,6-dihydrophenanthridines in up to 88% preparative yield. Under similar conditions, secondary phosphine sulfides form a difficult-to-separate mixture of N -vinylation/ C -phosphorylation products and adducts of phosphine sulfides with acetylenic ketones, while bis(2-phenylethyl)phosphine selenide gives only an adduct with acetylenic ketone in 78% yield.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-023-3859-5