Issue 9, 2022

Palladium-catalyzed denitrative N-arylation of nitroarenes with pyrroles, indoles, and carbazoles

Abstract

We have developed an efficient palladium-catalyzed denitrative N-arylation via cross-coupling of N–H heteroarenes with nitroarenes, one of the most inexpensive and fundamental feedstocks in the chemical industry. A variety of functionalized N-arylated heterocycles could be selectively synthesized in moderate to excellent yields. Furthermore, the success of the scale-up experiment and application in the late-stage modification of natural products and pharmaceutical derivatives showcased the synthetic potential of the direct denitrative N-arylation protocol in synthetic chemistry.

Graphical abstract: Palladium-catalyzed denitrative N-arylation of nitroarenes with pyrroles, indoles, and carbazoles

Supplementary files

Article information

Article type
Research Article
Submitted
04 Jan 2022
Accepted
10 Mar 2022
First published
11 Mar 2022

Org. Chem. Front., 2022,9, 2351-2356

Palladium-catalyzed denitrative N-arylation of nitroarenes with pyrroles, indoles, and carbazoles

L. Feng, J. Yao, L. Yu and W. Duan, Org. Chem. Front., 2022, 9, 2351 DOI: 10.1039/D2QO00010E

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