A Copper-Catalyzed Reductive Defluorination of β-Trifluoromethylated Enones via Oxidative Homocoupling of Grignard Reagents,Organic Letters

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A Copper-Catalyzed Reductive Defluorination of β-Trifluoromethylated Enones via Oxidative Homocoupling of Grignard Reagents
Organic Letters ( IF 4.9 ) Pub Date : 2018-03-07 00:00:00 , DOI: 10.1021/acs.orglett.8b00379
Xiaoting Wu ₁ , Fang Xie ₁ , Ilya D. Gridnev ₂ , Wanbin Zhang ₁

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An efficient copper-catalyzed reductive defluorination of β-trifluoromethylated enones via an oxidative homocoupling of Grignard reagents is reported. The reaction proceeded smoothly with a wide range of substrates, including the ones bearing aromatic heterocycles, such as furyl and thienyl ring systems in high yields (80–92%, except one example) under mild conditions. This provides a practical method for synthesis of gem-difluoroolefin ketones. It is also worth noting that this homocoupling process of Grignard reagents using β-trifluoromethylated enones as “oxidizing reagents” is effective for both the Csp²–Csp² and Csp³–Csp³ bond formations, including for substrates whose β-hydride elimination of the corresponding transition metal alkyl complex is particularly facile, affording coupling products with high yields (83–95%), simultaneously.

中文翻译：

格氏试剂的氧化均偶联反应对铜催化的β-三氟甲基化酮的还原脱氟

据报道，通过格氏试剂的氧化均偶联作用，铜可以有效地催化β-三氟甲基化烯酮的还原脱氟反应。在温和条件下，该反应可在多种底物上顺利进行，包括带有芳香杂环的底物，例如呋喃基和噻吩基环系，产率高（80–92％，一个例子除外）。这提供了合成宝石-二氟烯烃酮的实用方法。还值得注意的是，使用β-三氟甲基化的烯酮作为“氧化剂”的格氏试剂的均偶联过程对于Csp ² –Csp ²和Csp ³ –Csp ^{3均有效。} 形成的键，包括那些β-氢化物消除相应的过渡金属烷基络合物的底物特别容易，同时提供了高收率的偶联产物（83-95％）。

更新日期：2018-03-07

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