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Issue 20, 2020
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Access to 5H-benzo[a]carbazol-6-ols and benzo[6,7]cyclohepta[1,2-b]indol-6-ols via rhodium-catalyzed C–H activation/carbenoid insertion/aldol-type cyclization

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Abstract

The rhodium-catalyzed mono-ortho C–H activation/carbenoid insertion/aldol-type cyclization of 3-aldehyde-2-phenyl-1H-indoles with diazo compounds has been developed. This method provides a novel approach to 5H-benzo[a]carbazol-6-ols and benzo[6,7]cyclohepta[1,2-b]indol-6-ols with a broad range of substrate scope in an air atmosphere. In addition, the synthetic potentialities of the developed approach are demonstrated by gram scale and versatile late-stage transformations.

Graphical abstract: Access to 5H-benzo[a]carbazol-6-ols and benzo[6,7]cyclohepta[1,2-b]indol-6-ols via rhodium-catalyzed C–H activation/carbenoid insertion/aldol-type cyclization

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Article information


Submitted
10 Jul 2020
Accepted
25 Aug 2020
First published
27 Aug 2020

Org. Chem. Front., 2020,7, 3146-3159
Article type
Research Article

Access to 5H-benzo[a]carbazol-6-ols and benzo[6,7]cyclohepta[1,2-b]indol-6-ols via rhodium-catalyzed C–H activation/carbenoid insertion/aldol-type cyclization

Y. Yuan, X. Guo, X. Zhang, B. Li and Q. Huang, Org. Chem. Front., 2020, 7, 3146
DOI: 10.1039/D0QO00820F

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