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Issue 30, 2018
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Rhodium catalyzed cascade cyclization featuring B–H and C–H activation: one-step construction of carborane-fused N-polyheterocycles

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Abstract

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[b]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 cyclization, C–H activation, nucleophilic cyclization, dehydration and oxidative aromatization.

Graphical abstract: Rhodium catalyzed cascade cyclization featuring B–H and C–H activation: one-step construction of carborane-fused N-polyheterocycles

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Publication details

The article was received on 06 Apr 2018, accepted on 28 Jun 2018 and first published on 29 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC01568F
Chem. Sci., 2018,9, 6390-6394
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Rhodium catalyzed cascade cyclization featuring B–H and C–H activation: one-step construction of carborane-fused N-polyheterocycles

    H. Lyu, Y. Quan and Z. Xie, Chem. Sci., 2018, 9, 6390
    DOI: 10.1039/C8SC01568F

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