Selenium Transfer from Secondary Phosphine Selenides to Aminoacetylenic Ketones: Access to 1,2-Dihydro‑3H‑pyrrole-3-selones with a Stable CSe Bond

Secondary phosphine selenides were found to react with γ-aminoacetylenic ketones (80–85 °C, MeCN, 17–40 h) to afford 1,2-dihydro-3H-pyrrole-3-selones in 48–80% yields, products of unprecedented selenium transfer from the PSe bond to replace the carbonyl oxygen and to form dihydro-3H-pyrrole-3-selon...

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Bibliographic Details
Published in:Organic letters 2024-09, Vol.26 (35), p.7336-7340
Main Authors: Volkov, Pavel, Verkhoturova, Svetlana, Khrapova, Kseniya, Arbuzova, Svetlana, Bidusenko, Ivan, Albanov, Alexander, Trofimov, Boris
Format: Article
Language:English
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Summary:Secondary phosphine selenides were found to react with γ-aminoacetylenic ketones (80–85 °C, MeCN, 17–40 h) to afford 1,2-dihydro-3H-pyrrole-3-selones in 48–80% yields, products of unprecedented selenium transfer from the PSe bond to replace the carbonyl oxygen and to form dihydro-3H-pyrrole-3-selones having a CSe bond stable under ambient conditions.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02491