Oxidative Alkylarylation of N-Aryl Bicyclobutyl Amides with C(sp3)–H Feedstocks via C(sp3)–H/C(sp2)–H Functionalization
Jing Yuan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorJiao Zhou
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorPeng-Fei Xia
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
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 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
Jian-Hong Fan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
E-mail: [email protected]Search for more papers by this authorJing Yuan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorJiao Zhou
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
Search for more papers by this authorPeng-Fei Xia
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
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 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
Jian-Hong Fan
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan, 414006 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
The difunctionalization of bicyclo[1.1.0]butanes is an under-explored transformation that accesses to moieties that are otherwise difficult to prepare. Herein, a new oxidative radical alkylarylation of N-aryl bicyclobutyl amides with C(sp3)−H feedstocks is achieved in an atom-economic and photocatalyst- and light-free manner. This protocol follows a sequential C(sp3)–H/C(sp2)–H functionalization, providing an efficient route for diversity-oriented synthesis of functionalized 3-spirocyclobutyl oxindoles. In particular, a wide range of C(sp3)−H feedstocks, including ether, alcohol, amine, thioether, polychlorinated methane, silane, acetone, acetonitrile, toluene, and alkane are all suitable for the C(sp3)−H functionalization, demonstrating the broad applicability of this transformation.
Supporting Information
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