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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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Supplementary files

Article information


Submitted
06 Apr 2018
Accepted
28 Jun 2018
First published
29 Jun 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 6390-6394
Article type
Edge Article

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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