Issue 40, 2021

Discovery of a tetraarylhydrazine catalyst for electrocatalytic synthesis of imidazo-fused N-heteroaromatic compounds

Abstract

The development of electrocatalytic synthetic methods hinges on efficient molecular catalysts. Triarylamines are well-known redox catalysts because of the good stability of their corresponding amine radical cations. Herein we show that tris(4-(tert-butyl)phenyl)amine decomposes unexpectedly during electrolysis in MeOH/THF to afford a tetraarylhydrazine, 1,1,2,2-tetrakis(4-(tert-butyl)phenyl)hydrazine. In addition, we have applied this tetraarylhydrazine, which is either preprepared or formed in situ from tris(4-(tert-butyl)phenyl)amine, as an electrocatalyst for the synthesis of imidazopyridines and related N-heteroaromatic compounds through intramolecular [3 + 2] annulation. This metal-free electrocatalytic method provides straightforward access to the N-heteroaromatic compounds from readily available materials without the need for external chemical oxidants.

Graphical abstract: Discovery of a tetraarylhydrazine catalyst for electrocatalytic synthesis of imidazo-fused N-heteroaromatic compounds

Supplementary files

Article information

Article type
Paper
Submitted
22 aug 2021
Accepted
24 sep 2021
First published
29 sep 2021

Org. Biomol. Chem., 2021,19, 8789-8793

Discovery of a tetraarylhydrazine catalyst for electrocatalytic synthesis of imidazo-fused N-heteroaromatic compounds

Z. Hou, Z. Mao and H. Xu, Org. Biomol. Chem., 2021, 19, 8789 DOI: 10.1039/D1OB01644J

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