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

Boris A Trofimov; Pavel A Volkov; Kseniya O Khrapova; Anton A Telezhkin; Nina I Ivanova; Alexander I Albanov; Nina K Gusarova; Oleg N Chupakhin

doi:10.1039/C8CC01155A

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

Chem Commun (Camb). 2018 Mar 29;54(27):3371-3374. doi: 10.1039/C8CC01155A.

Authors

Boris A Trofimov¹, Pavel A Volkov¹, Kseniya O Khrapova¹, Anton A Telezhkin¹, Nina I Ivanova¹, Alexander I Albanov¹, Nina K Gusarova¹, Oleg N Chupakhin²

Affiliations

¹ A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation. [email protected].
² I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi/Akademicheskaya St., Ekaterinburg 620219, Russian Federation.

PMID: 29543294
DOI: 10.1039/C8CC01155A

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.