Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light,Chemical Science

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Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light
Chemical Science ( IF 7.6 ) Pub Date : 2022-06-15 , DOI: 10.1039/d2sc02291e
Wan-Lei Yu _{1,

2} , Zi-Gang Ren ₁ , Ke-Xing Ma ₁ , Hui-Qing Yang ₃ , Jun-Jie Yang ₁ , Haixue Zheng ₄ , Wangsuo Wu ₂ , Peng-Fei Xu _{1,

2,

4}

Affiliation

The transformations that allow the direct removal of hydrogen from their corresponding saturated counterparts by the dehydrogenative strategy are a dream reaction that has remained largely underexplored. In this report, a straightforward and robust cobaloxime-catalyzed photochemical dehydrogenation strategy via intramolecular HAT is described for the first time. The reaction proceeds through an intramolecular radical translocation followed by the cobalt assisted dehydrogenation without needing any other external photosensitizers, noble-metals or oxidants. With this approach, a series of valuable unsaturated compounds such as α,β-unsaturated amides, enamides and allylic and homoallylic sulfonamides were obtained in moderate to excellent yields with good chemo- and regioselectivities, and the synthetic versatility was demonstrated by a range of transformations. And mechanistic studies of the method are discussed.

中文翻译：

可见光下钴催化自由基易位化学选择性脱氢

通过脱氢策略从相应的饱和对应物中直接去除氢的转变是一个梦想的反应，但在很大程度上仍未得到充分探索。在本报告中，首次描述了一种通过分子内 HAT 的简单而稳健的钴肟催化光化学脱氢策略。该反应通过分子内自由基易位进行，然后进行钴辅助脱氢，不需要任何其他外部光敏剂、贵金属或氧化剂。通过这种方法，以中等至优异的产率获得了一系列有价值的不饱和化合物，例如α，β-不饱和酰胺、烯酰胺以及烯丙型和高烯丙型磺酰胺，具有良好的化学和区域选择性，并且通过一系列转化证明了合成的多功能性。并讨论了该方法的机理研究。

更新日期：2022-06-15

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