Enantioselective Palladium-Catalyzed Cross-Coupling of α-Bromo Carboxamides and Aryl Boronic Acids
Bowen Li
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorTiejun Li
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorMuinat A. Aliyu
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorProf. Dr. Zhen Hua Li
Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Handan Road 220, Shanghai, 200438 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wenjun Tang
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorBowen Li
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorTiejun Li
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorMuinat A. Aliyu
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorProf. Dr. Zhen Hua Li
Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Handan Road 220, Shanghai, 200438 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wenjun Tang
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorGraphical Abstract
A palladium catalyst loading as low as 0.5 mol % enables the cross-coupling of α-bromo carboxamides and aryl boronic acids, generating a series of chiral α-aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in suppressing the formation of biaryl side products.
Abstract
We herein report an enantioselective palladium-catalyzed cross-coupling between α-bromo carboxamides and aryl boronic acids, generating a series of chiral α-aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in overcoming the second transmetalation issue and allows the first asymmetric palladium-catalyzed coupling of α-bromo carbonyl compounds.
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