Direct Synthesis of Adipic Esters and Adiponitrile via Photoassisted Cobalt-Catalyzed Alkene Hydrodimerization |
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Authors: | Cheng Ren Guanghao Ji Xiankai Li Prof Jing Zhang |
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Institution: | The Institute for Advanced Studies, Wuhan University, 299 Bayi Rd, 430072 Wuhan, P. R. China |
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Abstract: | The direct hydrodimerization of acrylates and acrylonitrile offers a general streamlined access to industrially important intermediates to nylon 6,6. However, a practical catalytic method for this process has thus far underdeveloped owing to the challenges in regioselectivity and environmental compatibility of applied reagents. Here, we report a cobalt-catalyzed tail-to-tail hydrodimerization of activated alkenes driven by a visible-light photoredox catalysis at ambient temperature, which is applicable to both adipates and adiponitrile synthesis from potentially renewable feedstocks. This protocol utilizes half equivalent of hantzsch ester as a recyclable two-electron and two-proton donor with the assistance of catalytic amount of base as a proton shuttle, and has been shown to be highly regioselective and efficient for hydrodimerizing various activated alkenes to 1,4-difunctionalized butane derivatives. |
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Keywords: | adipate adiponitrile cobalt hydrodimerization photochemistry |
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