Issue 15, 2022

1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts

Abstract

A new synthetic approach to π-extended imidazolium salts is developed based on 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with imidoyl chlorides, where the key to the successful conversion is the addition of cesium fluoride as an additive. Experimental and theoretical studies revealed that this cycloaddition proceeds via a stepwise mechanism rather than a concerted mechanism. This present method provides an efficient method to synthesize a variety of imidazolium-containing polycyclic aromatic compounds.

Graphical abstract: 1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts

Supplementary files

Article information

Article type
Research Article
Submitted
15 Jun 2022
Accepted
17 Jun 2022
First published
29 Jun 2022

Org. Chem. Front., 2022,9, 4128-4134

1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts

Q. Li, Y. Hamamoto, C. C. H. Tan, H. Sato and S. Ito, Org. Chem. Front., 2022, 9, 4128 DOI: 10.1039/D2QO00941B

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