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Electroreduction Enables Regioselective 1,2-Diarylation of Alkenes with Two Electrophiles |
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| Authors: | Weijie Yu Shengchun Wang Meng He Zhou Jiang Yi Yu Jinping Lan Jin Luo Pengjie Wang Prof. Xiaotian Qi Prof. Tao Wang Prof. Aiwen Lei |
| Affiliation: | 1. National Research Center for Carbohydrate Synthesis, Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang, 330022, Jiangxi P. R. China These authors contributed equally to this work.;2. The Institute for Advanced Studies (IAS) and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, Hubei P. R. China;3. National Research Center for Carbohydrate Synthesis, Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang, 330022, Jiangxi P. R. China |
| Abstract: | Precisely introducing two similar functional groups into bulk chemical alkenes represents a formidable route to complex molecules. Especially, the selective activation of two electrophiles is in crucial demand, yet challenging for cross-electrophile-coupling. Herein, we demonstrate a redox-mediated electrolysis, in which aryl nitriles are both aryl radical precursors and redox-mediators, enables an intermolecular alkene 1,2-diarylation with a remarkable regioselectivity, thereby avoiding the involvement of transition-metal catalysts. This transformation utilizes cyanoarene radical anions for activating various aryl halides (including iodides, bromides, and even chlorides) and affords 1,2-diarylation adducts in up to 83 % yield and >20 : 1 regioselectivity with more than 80 examples, providing a feasible approach to complex bibenzyl derivatives. |
| Keywords: | Arylation Difunctionalization Electrochemistry Redox Catalysis Reductive Cross-Coupling |