Issue 23, 2020

Dearomative [4 + 2] annulations between 3-nitroindoles and enals through oxidative N-heterocyclic carbene catalysis

Abstract

Hydrocarbazolone and its derivatives are attractive organic molecules, which have been widely applied in the synthesis of natural products and pharmaceuticals. Herein, we describe a novel intermolecular dearomative [4 + 2] annulation of 3-nitroindoles and enals under oxidative N-heterocyclic carbene catalysis. With this organocatalytic strategy, a variety of dearomatised hydrocarbazolone products were obtained in high yields. This protocol was also suitable for the oxidative cyclisation of 2-nitrobenzothiophenes with enals, thereby affording a collection of 4-hydroxyldibenothiophenes.

Graphical abstract: Dearomative [4 + 2] annulations between 3-nitroindoles and enals through oxidative N-heterocyclic carbene catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
21 Jul 2020
Accepted
11 Aug 2020
First published
12 Aug 2020

Org. Chem. Front., 2020,7, 3862-3867

Dearomative [4 + 2] annulations between 3-nitroindoles and enals through oxidative N-heterocyclic carbene catalysis

H. Huang, Q. Li, Y. Liu, H. Leng, P. Xiang, Q. Dai, X. He, W. Huang and J. Li, Org. Chem. Front., 2020, 7, 3862 DOI: 10.1039/D0QO00868K

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