Issue 16, 2019

Palladium-catalyzed tandem one-pot synthesis of π-expanded imidazoles through a sequential Heck and oxidative amination reaction

Abstract

An efficient palladium-catalyzed route for tandem synthesis of imidazole-fused polyheterocycles from 2-vinyl imidazoles and aryl halides is described. The sequentially accomplished process comprises intermolecular Heck arylation of 2-vinyl imidazoles followed by an intramolecular aerobic oxidative C–H amination reaction promoted by the same Pd catalyst. This Pd-catalyzed tandem approach offers a straightforward protocol for the assembly of benzimidazo/phenanthroimidazo[1,2-a]quinolines in moderate to high yields, serving as a useful tool for the discovery of fluorescent materials.

Graphical abstract: Palladium-catalyzed tandem one-pot synthesis of π-expanded imidazoles through a sequential Heck and oxidative amination reaction

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2019
Accepted
29 Mar 2019
First published
30 Mar 2019

Org. Biomol. Chem., 2019,17, 4014-4023

Palladium-catalyzed tandem one-pot synthesis of π-expanded imidazoles through a sequential Heck and oxidative amination reaction

X. Li, X. Chen, H. Wang, C. Chen, P. Sun, B. Mo and J. Peng, Org. Biomol. Chem., 2019, 17, 4014 DOI: 10.1039/C9OB00482C

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