Solvent‐Controlled Copper‐Catalyzed Radical Decarboxylative Coupling for Alkenyl C(sp2)−P Bond Formation,Asian Journal of Organic Chemistry

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Solvent‐Controlled Copper‐Catalyzed Radical Decarboxylative Coupling for Alkenyl C(sp2)−P Bond Formation
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2017-08-30 , DOI: 10.1002/ajoc.201700434
Lin Tang ₁ , Lixian Wen ₂ , Tian Sun ₁ , Di Zhang ₁ , Zhen Yang ₁ , Chengtao Feng ₃ , Zhiyong Wang ₂

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The first solvent‐controlled copper‐catalyzed oxidative decarboxylative coupling of alkenyl acids with P(O)H compounds for alkenyl C(sp²)−P bond formation by a free‐radical process is reported. The reaction enables the highly chemo‐ and stereoselective synthesis of various (E)‐alkenylphosphonates and (E)‐alkenylphosphinate oxides in moderate to good yields. On the basis of this catalytic system, styrenes and β‐nitrostyrene as well as alkenyl acids can also give the corresponding products by cross‐dehydrogenative coupling and denitration, respectively. By altering the oxidant, the oxyphosphorylation of styrenes with P(O)H compounds readily yields β‐ketophosphonates. The reaction described here enables a versatile and practical avenue for the formation of valuable C−P bonds.

中文翻译：

溶剂控制的铜催化自由基脱羧偶联，形成烯基C（sp2）-P键

据报道，首次通过溶剂控制的烯基酸与P（O）H化合物的铜催化氧化脱羧反应通过自由基过程形成了烯基C（sp ²）-P键。该反应可实现各种（E）-烯基膦酸酯和（E的高化学和立体选择性合成）-烯基次膦酸酯氧化物，产率中等至良好。在这种催化体系的基础上，苯乙烯和β-硝基苯乙烯以及烯基酸也可以分别通过交叉脱氢偶联和脱硝作用得到相应的产物。通过改变氧化剂，苯乙烯与P（O）H化合物的氧基磷酸化很容易产生β-酮膦酸酯。此处描述的反应为形成有价值的C-P键提供了一种通用且实用的途径。

更新日期：2017-08-30

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