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Regio-selective synthesis of diversely substituted benzo[a]carbazoles through Rh(iii)-catalyzed annulation of 2-arylindoles with α-diazo carbonyl compounds†
Bin Li,Beibei Zhang,Xinying Zhang,Xuesen Fan
Chemical Communications Pub Date : 12/22/2016 00:00:00 , DOI:10.1039/C6CC08377C
Abstract

A novel synthetic approach toward benzo[a]carbazoles or 6-amino benzo[a]carbazoles containing an unprotected NH unit through Rh(III)-catalyzed cascade reactions of 2-arylindoles or 2-arylindole-3-carbonitriles with α-diazo carbonyl compounds has been established. To our knowledge, this is the first example in which the NH unit of indole is used as a directing group for an intramolecular C(sp2)H bond functionalization to give benzo[a]carbazole derivatives. Notably, this method features easily obtainable substrates, good functional group tolerance, excellent regio-selectivity, and high atom-efficiency.

Graphical abstract: Regio-selective synthesis of diversely substituted benzo[a]carbazoles through Rh(iii)-catalyzed annulation of 2-arylindoles with α-diazo carbonyl compounds
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