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

James A Vogel; Kirya F Miller; Eunjeong Shin; Jenna M Krussman; Patrick R Melvin

doi:10.1039/d3ra06561h

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

RSC Adv. 2023 Oct 13;13(43):30129-30132. doi: 10.1039/d3ra06561h. eCollection 2023 Oct 11.

Authors

James A Vogel¹, Kirya F Miller¹, Eunjeong Shin¹, Jenna M Krussman¹, Patrick R Melvin¹

Affiliation

¹ Department of Chemistry, Bryn Mawr College Bryn Mawr Pennsylvania 19010 USA 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.