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Issue 27, 2018
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Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants

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Abstract

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.

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

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Publication details

The article was received on 13 Feb 2018, accepted on 05 Mar 2018 and first published on 06 Mar 2018


Article type: Communication
DOI: 10.1039/C8CC01155A
Citation: Chem. Commun., 2018,54, 3371-3374
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    Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants

    B. A. Trofimov, P. A. Volkov, K. O. Khrapova, A. A. Telezhkin, N. I. Ivanova, A. I. Albanov, N. K. Gusarova and O. N. Chupakhin, Chem. Commun., 2018, 54, 3371
    DOI: 10.1039/C8CC01155A

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