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

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, approx...

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Detalles Bibliográficos
Autores principales: Vogel, James A., Miller, Kirya F., Shin, Eunjeong, Krussman, Jenna M., Melvin, Patrick R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10573916/
https://www.ncbi.nlm.nih.gov/pubmed/37842679
http://dx.doi.org/10.1039/d3ra06561h
Descripción
Sumario: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.

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