The combination of N-heterocyclic carbene (NHC) organocatalysis with photochemical activation is becoming increasingly established as an approach for conducting radical organic reactions under mild and practical conditions. As comparatively easy to prepare and handle organic compounds, alkyl silanes are attractive substrates for radical chemistry as desilylative mesolysis of the corresponding radical cations is known to be rapid. Here, we report the successful application of benzyl silane derivatives as source of alkyl radicals in dual NHC/photoredox-catalyzed radical–radical coupling reactions with acyl fluorides. Relatively electron-rich benzyl silanes reacted smoothly to afford the corresponding ketones in generally good yields, while optimization of the NHC and photocatalyst allowed for a wider scope including primary benzyl substrates. Furthermore, initial experiments revealed that organosilanes bearing N-, O- and S-heteroatoms can also serve as alkyl radical sources under these conditions.

中文翻译：

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酰氟和烷基硅烷的双 N-杂环卡宾/光氧化还原催化偶联


N-杂环卡宾 （NHC） 有机催化与光化学活化的结合正日益成为在温和和实际条件下进行自由基有机反应的一种方法。由于相对容易制备和处理有机化合物，烷基硅烷是自由基化学的有吸引力的底物，因为已知相应自由基阳离子的去硅烷化介解速度很快。在这里，我们报道了苄基硅烷衍生物作为烷基自由基来源在与酰基氟化物的双重 NHC/光氧化还原催化的自由基-自由基偶联反应中的成功应用。相对富含电子的苄基硅烷反应顺利，以通常良好的产率得到相应的酮，而 NHC 和光催化剂的优化允许更广泛的范围，包括伯苄基底物。此外，初步实验表明，在这些条件下，带有 N-、O- 和 S-杂原子的有机硅烷也可以用作烷基自由基源。