Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone |
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Authors: | Qing Liu Shuchen Yu Liangzhen Hu Muhamad Ijaz Hussain Xiaohui Zhang Yan Xiong |
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Institution: | 1. School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China;2. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China |
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Abstract: | The cross-dehydrogenative coupling strategy for metal-free phosphonation and cyanation of secondary N-alkyl anilines has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to imine formation, then to respective α-aminophosphonates and α-aminonitriles was proposed. |
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Keywords: | α-aminonitriles α-aminophosphonates Anilines Cyanation Oxidation |
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