Issue 10, 2019

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
14 Jän 2019
Accepted
16 Feb 2019
First published
21 Feb 2019

Org. Biomol. Chem., 2019,17, 2818-2823

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

K. Sato, G. Sandford, Y. Konishi, N. Yanada, C. Toda, A. Tarui and M. Omote, Org. Biomol. Chem., 2019, 17, 2818 DOI: 10.1039/C9OB00097F

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