Rh(III)-catalyzed C8 arylation of quinoline N-oxides with arylboronic acids |
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| Affiliation: | 1. State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China;2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China;1. Department of Traditional Chinese Medicine, Jilin Agricultural University, Changchun 130118, China;2. Institute of Medicinal Plant Development, Chinese Academy of Medical Science & Peking Union Medical College Beijing 100193, China;1. Laboratory for Medicinal Chemistry and Natural Products, Lebanese University, Faculty of Sciences (1) and PRASE-EDST, Hadath, Beirut, Lebanon;2. Université de Rennes 1, Institut des Sciences Chimiques, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France;1. Chinese Academy of Sciences Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Shanghai 201203, China;2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China;3. University of Chinese Academy of Sciences, Beijing 100049, China;4. School of Pharmaceutical Science, Shanxi Medical University, Taiyuan 030001, China;1. YMU-HKBU Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Yuehua Street, Kunming 650500, China;2. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Weijing Road, Tianjin 300071, China |
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| Abstract: | Herein, we report the first RhIII-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners. This procedure is simple, and the reaction shows perfect regioselectivity, a broad substrate scope, and isolated yields of up to 92%. We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide. |
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| Keywords: | C8 arylation Arylboronic acids Regioselectivity |
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