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Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants

Pyridines undergo site selective cross-coupling with secondary phosphine chalcogenides (oxides, sulfides, and selenides) in the presence of acylphenylacetylenes under metal-free mild conditions (70-75 °C, MeCN) to afford 4-chalcogenophosphoryl pyridines in up to 71% yield. In this new type of SNHAr...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (27), p.3371-3374
Main Authors: Trofimov, Boris A, Volkov, Pavel A, Khrapova, Kseniya O, Telezhkin, Anton A, Ivanova, Nina I, Albanov, Alexander I, Gusarova, Nina K, Chupakhin, Oleg N
Format: Article
Language:English
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Summary:Pyridines undergo site selective cross-coupling with secondary phosphine chalcogenides (oxides, sulfides, and selenides) in the presence of acylphenylacetylenes under metal-free mild conditions (70-75 °C, MeCN) to afford 4-chalcogenophosphoryl pyridines in up to 71% yield. In this new type of SNHAr reaction acylacetylenes act as oxidants, being stereoselectively reduced to the corresponding olefins of the E-configuration.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc01155a