Synergistic Pd/Cu catalysis enabled cross-coupling of glycosyl stannanes with sulfonium salts to access C-aryl/alkenyl glycals |
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| Institution: | 1. Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China;2. National Engineering Research Center of Chemical Fertilizer Catalyst, College of Chemical Engineering, Fuzhou University, Fuzhou 350108, China;3. Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China;4. Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Fudan University, Shanghai 200433, China;1. State Key Laboratory of Molecular Vaccinology and Molecular Diagnostics & Center for Molecular Imaging and Translational Medicine, School of Public Health, Xiamen University, Xiamen 361102, China;2. State Key Laboratory of Cellular Stress Biology, Innovation Center for Cell Biology, School of Life Sciences, Xiamen University, Xiamen 361102, China;1. School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051, China;2. Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China;3. School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, China;1. State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, College of Life Sciences and KLMDASR of Tianjin, Nankai University, Tianjin 300353, China;2. School of Chemistry, Tiangong University, Tianjin 300387, China |
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| Abstract: | A highly efficient coupling of glycosyl stannanes and sulfonium salts enabled by synergistic Pd/Cu catalysis is disclosed, facilitating the construction of C-aryl/alkenyl glycals under mild conditions in high yields. The protocol tolerates a wide scope of functional groups including ketone, cyano, ester, amide, nitro, halide. The one-pot formal C H glycosylation starting from arene is demonstrated with a reaction sequence of dibenzothiophenylation/Stille coupling. Besides, a gram-scale reaction is performed successfully, showing the high applicability of this protocol. |
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