Palladium-catalyzed cross-coupling reactions of aryl boronic acids with aryl halides in water |
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| Authors: | Shaoyan WANG Zhiqiang ZHANG Zhizhi HU Yue WANG Peng LEI Haijun CHI |
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| Institution: | 1. Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-C.S.I.C., Facultad de Ciencias, Campus San Francisco, E-50009 Zaragoza, Spain;2. Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-C.S.I.C., Escuela de Ingeniería y Arquitectura, Ed. Torres Quevedo, Campus Río Ebro, E-50018 Zaragoza, Spain;1. College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China;2. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;3. Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China;4. Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China;1. Hungarian Academy of Sciences, Research Centre for Natural Sciences, Institute of Organic Chemistry, 1519 Budapest, P.O.B. 286, Hungary;2. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, P.O.B. 91, Hungary;3. Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, 1475 Budapest, P.O.B. 100, Hungary;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 Chemical and Materials Engineering, National Yunlin University of Science and Technology, Yunlin 64002, Taiwan, Republic of China;2. Department of Chemical Engineering, National Cheng Kung University, Tainan 70101, Taiwan, Republic of China |
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| Abstract: | An efficient Suzuki cross-coupling reaction using a variety of aryl halides in neat water was developed. The Pd-catalyzed reaction between aryl bromides or chlorides and phenyl bo-ronic acids was compatible with various functional groups and affords biphenyls in good to excellent yields without requirement of organic cosolvents. The air stability and solubility in water of the palladium-phosphinous acid complexes were considered to facilitate operation of the coupling reaction and product isolation. The reaction conditions including Pd catalyst selection, temperature, base and catalyst recoverability were also investigated. |
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