A Modified Beckmann Rearrangement for the Facile Synthesis of Amidines and Imidates via Imidoyl Fluoride Intermediates

Authors

James A. Vogel, Bryn Mawr College
Kirya Miller, Bryn Mawr College
Eunjeong Shin, Bryn Mawr College
Jenna Krussman, Bryn Mawr College
Patrick R. Melvin, Bryn Mawr CollegeFollow

Document Type

Article

Version

Final Published Version

Publication Title

RSC Advances

Volume

13

Publication Date

2023

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.

Citation

Vogel, James, Kirya Miller, Eunjeong Shin, Jenna Krussman, and Patrick Melvin. 2023. “A Modified Beckmann Rearrangement for the Facile Synthesis of Amidines and Imidates via Imidoyl Fluoride Intermediates.” RSC Advances 13 (43): 30129–32. https://doi.org/10.1039/D3RA06561H.

DOI

https://doi.org/10.1039/D3RA06561H