A general method for the synthesis of 5-difluoromethyl isoxazoles. Issue 52 (24th December 2020)

• Record Type: Journal Article
• Authors: Lin, Jiawei; Wu, Wei; Weng, Zhiqiang
• Is Part Of: Tetrahedron letters. Volume 61:Issue 52(2020)
• Publication Date: 2020-12-24
• Subjects: Fluorine -- Difluoromethylation -- Vinyl azides -- Denitrogenative cyclization -- Synthetic methods; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152672
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A method for synthesis of 5-(chloro)difluoromethyl isoxazoles was developed. Various 5-(chloro)difluoromethyl isoxazoles were isolated in moderate to excellent yields. A variety of functional groups were tolerated. Abstract: An efficient reaction of vinyl azides with difluoroacetic anhydride or chlorodifluoroacetic anhydride has been developed. It involved sequential difluoroacetylation of vinyl azides, followed by deprotonation, cyclization, and dinitrogen elimination, providing a convenient synthesis of both 5-difluoromethyl and 5-chlorodifluoromethyl isoxazoles at yields up to 89%.