Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay

Xiang-Huan Shan, Hong-Xing Zheng, Bo Yang, Lin Tie, Jia-Le Fu, Jian-Ping Qu () and Yan-Biao Kang ()
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Xiang-Huan Shan: University of Science and Technology of China
Hong-Xing Zheng: University of Science and Technology of China
Bo Yang: University of Science and Technology of China
Lin Tie: University of Science and Technology of China
Jia-Le Fu: University of Science and Technology of China
Jian-Ping Qu: Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University
Yan-Biao Kang: University of Science and Technology of China

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Base-promoted C-H cleavage without transition metals opens a practical alternative for the one based on noble metals or radical initiators. The resulting carbanion can pass through radical addition to unsaturated bonds like C-N or C-C triple bonds, in which stoichiometric oxidants are needed. When in situ C-H cleavage meets catalytic carbanion-radical relay, it turns to be challenging but has not been accomplished yet. Here we report the combination of base-promoted benzylic C-H cleavage and copper-catalyzed carbanion-radical redox relay. Catalytic amount of naturally abundant and inexpensive copper salt, such as copper(II) sulfate, is used for anion-radical redox relay without any external oxidant. By avoiding using N-O/N-N homolysis or radical initiators to generate iminyl radicals, this strategy realizes modular synthesis of N-H indoles and analogs from abundant feedstocks, such as toluene and nitrile derivatives, and also enables rapid synthesis of large scale pharmaceuticals.

Date: 2019
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DOI: 10.1038/s41467-019-08849-z

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