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One-pot access to tetrahydrobenzo[c]carbazoles from simple ketones by using O2 as an oxidant

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Abstract

An effective and operationally simple one-pot Brønsted acid catalyzed cascade method is demonstrated for the synthesis of diversely functionalized carbazole frameworks starting from protecting group free 2-alkenyl indoles. The employment of easily available unactivated ketones as annulating partners, mostly unexplored for the synthesis of carbazoles, is the major highlight of this protocol. This protocol is step- and atom-economical, uses molecular oxygen as the green oxidant, and gives water as the only by-product and is amenable to different functional groups. Moreover, gram-scale synthesis and downstream modification of the obtained products demonstrate the synthetic applicability of this protocol.

Graphical abstract: One-pot access to tetrahydrobenzo[c]carbazoles from simple ketones by using O2 as an oxidant

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Article information


Submitted
27 Dec 2019
Accepted
06 Feb 2020
First published
08 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

One-pot access to tetrahydrobenzo[c]carbazoles from simple ketones by using O2 as an oxidant

S. Saha and M. S. Maji, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02751C

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