Issue 43, 2023, Issue in Progress
From the journal:

RSC Advances

A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates†

James A. Vogel,a   Kirya F. Miller,a   Eunjeong Shin,a   Jenna M. Krussmana  and  Patrick R. Melvin ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010, USA
E-mail: prmelvin@brynmawr.edu

Abstract

Herein, we report a modified Beckmann rearrangement using sulfone iminium fluoride (SIF) reagents to rapidly synthesize imidoyl fluoride intermediates. Subsequently, amidine and imidate products can be formed following the introduction of amine and alcohol nucleophiles, respectively. Overall, approximately 50 amidine and imidate products have been isolated in high yields utilizing mild conditions.

Graphical abstract: A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates

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Article information

DOI
https://doi.org/10.1039/D3RA06561H
Article type
Paper
Submitted
26 Sep 2023
Accepted
04 Oct 2023
First published
13 Oct 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 30129-30132

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A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates

J. A. Vogel, K. F. Miller, E. Shin, J. M. Krussman and P. R. Melvin, RSC Adv., 2023, 13, 30129 DOI: 10.1039/D3RA06561H

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