Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters
Kai Wu
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
HKU Shenzhen Institute of Research & Innovation, Shenzhen, China
Search for more papers by this authorDr. Liang-Liang Wu
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
Search for more papers by this authorCorresponding Author
Dr. Cong-Ying Zhou
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
HKU Shenzhen Institute of Research & Innovation, Shenzhen, China
Present address: College of Chemistry and Materials Science, Jinan University, Guangzhou, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Chi-Ming Che
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
HKU Shenzhen Institute of Research & Innovation, Shenzhen, China
Search for more papers by this authorKai Wu
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
HKU Shenzhen Institute of Research & Innovation, Shenzhen, China
Search for more papers by this authorDr. Liang-Liang Wu
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
Search for more papers by this authorCorresponding Author
Dr. Cong-Ying Zhou
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
HKU Shenzhen Institute of Research & Innovation, Shenzhen, China
Present address: College of Chemistry and Materials Science, Jinan University, Guangzhou, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Chi-Ming Che
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
HKU Shenzhen Institute of Research & Innovation, Shenzhen, China
Search for more papers by this authorAbstract
A transition-metal-free C(sp2)−C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.
Conflict of interest
The authors declare no conflict of interest.
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