以酰基乙炔为氧化剂实现吡啶与二硫代次膦酸酯的无金属位点选择性交叉偶联反应。
Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants.
作者信息
Trofimov Boris A, Volkov Pavel A, Khrapova Kseniya O, Telezhkin Anton A, Ivanova Nina I, Albanov Alexander I, Gusarova Nina K, Chupakhin Oleg N
机构信息
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation.
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.
出版信息
Chem Commun (Camb). 2018 Mar 29;54(27):3371-3374. doi: 10.1039/C8CC01155A.
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.
在无金属温和条件下（70 - 75 °C，乙腈），吡啶能与仲膦硫属化物（氧化物、硫化物和硒化物）在酰基苯乙炔存在下发生位点选择性交叉偶联反应，以高达71%的产率得到4 - 硫属磷酰基吡啶。在这种新型的亲核芳香取代反应（SNHAr）中，酰基乙炔作为氧化剂，被立体选择性地还原为E - 构型的相应烯烃。
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