Lewis acid promoted fluorine-alkoxy group exchange reactions for the synthesis of 5-alkoxy-4,4-difluoroisoxazoline systems

Sato, Kazuyuki; Sandford, Graham; Konishi, Yukiko; Yanada, Niko; Toda, Chisako; Tarui, Atsushi; Omote, Masaaki

doi:10.1039/c9ob00097f

Lewis acid promoted fluorine-alkoxy group exchange reactions for the synthesis of 5-alkoxy-4,4-difluoroisoxazoline systems

Sato, Kazuyuki; Sandford, Graham; Konishi, Yukiko; Yanada, Niko; Toda, Chisako; Tarui, Atsushi; Omote, Masaaki

Authors

Kazuyuki Sato

Graham Sandford

Yukiko Konishi

Niko Yanada

Chisako Toda

Atsushi Tarui

Masaaki Omote

Abstract

Fluorine-alkoxy group exchange reactions of fluorinated isoxazoline derivatives promoted by Lewis acids to give various 5-alkoxylated 4,4-difluoroisoxazolines via SN1 type processes in good to excellent yields are reported. Sterically demanding phenol substrates such as 2,6-diphenylphenol gave novel aryl substituted products via electrophilic aromatic substitution.

Citation

Sato, K., Sandford, G., Konishi, Y., Yanada, N., Toda, C., Tarui, A., & Omote, M. (2019). Lewis acid promoted fluorine-alkoxy group exchange reactions for the synthesis of 5-alkoxy-4,4-difluoroisoxazoline systems. Organic and Biomolecular Chemistry, 17(10), 2818-2823. https://doi.org/10.1039/c9ob00097f

Journal Article Type	Article
Acceptance Date	Feb 16, 2019
Online Publication Date	Feb 21, 2019
Publication Date	Mar 14, 2019
Deposit Date	Feb 21, 2019
Publicly Available Date	Feb 16, 2020
Journal	Organic and Biomolecular Chemistry
Print ISSN	1477-0520
Electronic ISSN	1477-0539
Publisher	Royal Society of Chemistry
Peer Reviewed	Peer Reviewed
Volume	17
Issue	10
Pages	2818-2823
DOI	https://doi.org/10.1039/c9ob00097f