C−H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes,Angewandte Chemie International Edition

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C−H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-09 , DOI: 10.1002/anie.201914226
Leonardo Massignan ₁ , Xuefeng Tan ₁ , Tjark H Meyer ₁ , Rositha Kuniyil ₁ , Antonis M Messinis ₁ , Lutz Ackermann ₁

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The catalytic generation of hypervalent iodine(III) reagents by anodic electrooxidation was orchestrated towards an unprecedented electrocatalytic C−H oxygenation of weakly coordinating aromatic amides and ketones. Thus, catalytic quantities of iodoarenes in concert with catalytic amounts of ruthenium(II) complexes set the stage for versatile C−H activations with ample scope and high functional group tolerance. Detailed mechanistic studies by experiment and computation substantiate the role of the iodoarene as the electrochemically relevant species towards C−H oxygenations with electricity as a sustainable oxidant and molecular hydrogen as the sole by‐product. para‐Selective C−H oxygenations likewise proved viable in the absence of directing groups.

中文翻译：

电生高价碘和钌配合物双重催化实现的 C−H 氧化反应

通过阳极电氧化催化生成高价碘 (III) 试剂，旨在实现弱配位芳香酰胺和酮前所未有的电催化 C−H 氧化。因此，碘芳烃的催化量与钌(II)配合物的催化量相结合，为具有广泛范围和高官能团耐受性的多功能CH活化奠定了基础。通过实验和计算进行的详细机理研究证实了碘芳烃作为电化学相关物种在 C−H 氧化反应中的作用，其中电作为可持续的氧化剂，分子氢作为唯一的副产物。对位选择性 C−CH 氧化同样被证明在没有导向基团的情况下是可行的。

更新日期：2020-01-10

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