biostudies-literatureLyu HNational Natural Science Foundation of China6390-6394https://www.ebi.ac.uk/biostudies/studies/S-EPMC6115682biostudies-literatureUnknown9(30)A one-pot strategy for efficient and facile synthesis of C,B-substituted carborane-fused N-polyheterocycles is reported. A rhodium catalyzed cascade cyclization of carboranyl N-arylimines with vinyl ketones enables the effective construction of three new B-C and C-C bonds in one reaction. Both carboranyl B-H and aryl C-H bonds are sequentially activated, leading to a series of previously unavailable C,B-substituted carborane-fused cyclopenta[<i>b</i>]quinoline derivatives, for potential applications in pharmaceuticals and materials, in a step-economical manner. The successful isolation and structural identification of a key intermediate provide solid evidence for the reaction mechanism, involving a tandem sequence of regioselective B-H activation, alkene insertion, nucleophilic cyclizationChemical scienceRhodium catalyzed cascade cyclization featuring B-H and C-H activation: one-step construction of carborane-fused N-polyheterocycles.PMC6115682N_CUHK442/14Lyu HXie ZQuan YfalseRhodium catalyzed cascade cyclization featuring B-H and C-H activation: one-step construction of carborane-fused N-polyheterocycles.A one-pot strategy for efficient and facile synthesis of C,B-substituted carborane-fused N-polyheterocycles is reported. A rhodium catalyzed cascade cyclization of carboranyl N-arylimines with vinyl ketones enables the effective construction of three new B-C and C-C bonds in one reaction. Both carboranyl B-H and aryl C-H bonds are sequentially activated, leading to a series of previously unavailable C,B-substituted carborane-fused cyclopenta[<i>b</i>]quinoline derivatives, for potential applications in pharmaceuticals and materials, in a step-economical manner. The successful isolation and structural identification of a key intermediate provide solid evidence for the reaction mechanism, involving a tandem sequence of regioselective B-H activation, alkene insertion, nucleophilic cyclization2018-01-01T00:00:00Z2018 Aug2025-04-22T12:52:13.406Z2019-03-27T00:01:47ZS-EPMC61156823031056710.1039/c8sc01568f