Visible-Light Induced and PIFA Enabled [4+2] Annulation of Alkenes with N-Aryl Substituted Hydroxamic Acids

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作者: Wang, Yu-Zhao Jiang, Menglu Zhang, Feng Zhang, Hua-Wei Wu, Yue Yu, Wei Li, Yan

作者单位: ^cShanghai Advanced Research Institute, Chinese Academy of Science, 99 Haike Road, Shanghai, 201210, China ^bState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Road, Lanzhou, 730000, China ^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong, Academy of Medical Sciences, 6699 Qingdao Road, Jinan, Shandong, 250117, China

关键词: Amidoxyl radicals Benzo[c]-[1,2]oxazines Hydroxamic acids Photo-oxidation [4+2] Annulations

摘要: In this paper, we reported a facile approach for the preparation of benzo[c][1,2]oxazine scaffolds via visible light induced phenyl iodine bis oxidative [4+2] annulation of vinyl benzenes with N-aryl substituted hydroxamic acids. In the transformation, amidoxyl radicals are readily generated via covalent I−O bond formation and photo-induced I−O cleavage from N-aryl substituted hydroxamic acids, and their coupling with vinyl arenes in the form of [4+2] annulation delivers benzo[c]-[1,2]oxazines ...更多; In this paper, we reported a facile approach for the preparation of benzo[c][1,2]oxazine scaffolds via visible light induced phenyl iodine bis oxidative [4+2] annulation of vinyl benzenes with N-aryl substituted hydroxamic acids. In the transformation, amidoxyl radicals are readily generated via covalent I−O bond formation and photo-induced I−O cleavage from N-aryl substituted hydroxamic acids, and their coupling with vinyl arenes in the form of [4+2] annulation delivers benzo[c]-[1,2]oxazines derivatives. This reaction proceeds in the absence of transition metals and catalysts, exhibiting broad substrate scope of both alkenes and N-aryl substituted hydroxamic acids.收起

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