Issue 84, 2023

Copper-catalyzed nitration of electron-deficient BN-naphthalene

Abstract

Under Cu-catalysis, a regioselective nitration of 1,8-dihalogenated BN-naphthalene (ABN) compounds (4a–4c) has been established with the use of tert-butyl nitrite as the nitrating reagent. The syntheses of dihalo-ABN nitro products (6a–6c; halo = Cl, Br and I) were case-studied in conjunction with the first synthesis and characterization of diiodo-ABN compound 4c. The molecular structures of these compounds have been spectroscopically characterized and further confirmed by X-ray single crystal diffraction experiments. This method allows direct regioselective nitration of electron-deficient ABN systems, providing a step-economical entry to novel nitro-ABN structural motifs with potential applications in agrochemicals, materials sciences, and the medicinal and pharmaceutical industries.

Graphical abstract: Copper-catalyzed nitration of electron-deficient BN-naphthalene

Supplementary files

Article information

Article type
Communication
Submitted
03 Sep 2023
Accepted
26 Sep 2023
First published
30 Sep 2023

Chem. Commun., 2023,59, 12581-12584

Copper-catalyzed nitration of electron-deficient BN-naphthalene

X. Fang, Chem. Commun., 2023, 59, 12581 DOI: 10.1039/D3CC04359B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements