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Cu-Catalyzed aromatic C–H imidation with N-fluorobenzenesulfonimide: mechanistic details and predictive models

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Brandon E. Haines, Takahiro Kawakami, Keiko Kuwata, Kei Murakami, Kenichiro Itami and Djamaladdin G. Musaev

Chem. Sci. 2016, Advance article. DOI: 10.1039/C6SC04145K

The CuBr-catalyzed C–H imidation of arenes, previously reported by us, utilizes an inexpensive catalyst and is applicable to a broad scope of complex arenes. The computational and experimental study reported here shows that the mechanism of the reaction is comprised of two parts: (1) generation of the active dinuclear CuII–CuII catalyst; and (2) the catalytic cycle for the C–H bond imidation of arenes. A simple predictive tool was developed and experimentally validated to determine the regiochemical outcome for a given substrate.

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