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Herein, we have realized an efficient and solvent-tunable Rh(III)-catalyzed [5+2] annulation of N-benzo[d]imidazole indolines with 2,2-difluorovinyl tosylate that presented an unusual 1,2-regioselectivity for the chemodivergent construction of monofluorinated and gem-difluorinated benzodiazepines, which was defined as potent anti-tumor agents against different cancer cell lines. In general, this work provides a powerful complement to both C-H activation chemistry and anti-tumor lead discovery.
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