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

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
• Public URL: https://durham-repository.worktribe.com/output/1307413