Majhi Jadab, Granados Albert, Matsuo Bianca, Ciccone Vittorio, Dhungana Roshan K, Sharique Mohammed, Molander Gary A
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA
Chem Sci. 2023 Jan 3;14(4):897-902. doi: 10.1039/d2sc05918e. eCollection 2023 Jan 25.
The synthetic application of (hetero)aryl radicals in organic synthesis has been known since the last century. However, their applicability has significantly suffered from ineffective generation protocols. Herein, we present a visible-light-induced transition metal-free (hetero)aryl radical generation from readily available (hetero)aryl halides for the synthesis of 3,3'-disubstituted oxindoles. This transformation is amenable to a wide range of (hetero)aryl halides as well as several easily accessible acrylamides, and it is also scalable to multigram synthesis. Finally, the versatility of the oxindole products is demonstrated through their conversion to a variety of useful intermediates applicable to target-directed synthesis.
（杂）芳基自由基在有机合成中的应用自上世纪以来就已为人所知。然而，它们的适用性因生成方法效率低下而受到显著影响。在此，我们展示了一种由易得的（杂）芳基卤化物通过可见光诱导的无过渡金属（杂）芳基自由基生成反应，用于合成3,3'-二取代的氧化吲哚。这种转化适用于多种（杂）芳基卤化物以及几种易于获得的丙烯酰胺，并且还可扩展至克级规模的合成。最后，通过将氧化吲哚产物转化为适用于目标导向合成的各种有用中间体，证明了其多功能性。
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