Copper-Catalyzed Regioselective Cyanation/Diarylmethylation of Formamides: Construction of α-Cyano Functionalized Tetra-Substituted Olefins
Minjing Yuan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
These authors contributed equally to this work.
Search for more papers by this authorZikang Li
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China
These authors contributed equally to this work.
Search for more papers by this authorWeifeng Xu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Biquan Xiong
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorYu Liu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Min Liu
School of Chemistry and Materials Engineering, Huizhou University, Huizhou, Guangdong, 516007 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorKe-Wen Tang
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Longzhi Zhu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorMinjing Yuan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
These authors contributed equally to this work.
Search for more papers by this authorZikang Li
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China
These authors contributed equally to this work.
Search for more papers by this authorWeifeng Xu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Biquan Xiong
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorYu Liu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Min Liu
School of Chemistry and Materials Engineering, Huizhou University, Huizhou, Guangdong, 516007 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorKe-Wen Tang
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorCorresponding Author
Longzhi Zhu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
A copper-catalyzed cyanation/diarylmethylation of formamides has been developed for the synthesis of α-cyano functionalized tetra-substituted olefins by utilizing para-quinone methides (p-QMs) and trimethylcyanosilane as functionalization sources. Various kinds of p-QMs and formamides are well tolerated, delivering the desired products with 72%—94% yields, demonstrating broad functional group tolerance. Notably, the reaction does not require noble metals and proceeds regioselectively under mild conditions. Based on step-by-step control experiments, Hammett studies and DFT calculation, a plausible mechanism is proposed.
Supporting Information
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