Transformation of Alkynes into α- or β-Difluorinated Alkyl Azides by an Efficient One-Pot Two-Step Procedure.

Org Lett

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry , Northeast Normal University, Changchun 130024 , China.

Published: December 2019

Reported herein an unprecedented 1,2-azide migratory hydroazidation and subsequent -difluorination of alkynes accessing β-difluorinated alkyl azides. Importantly, functional group controlled 1,2-azide or 1,2-aryl migration was observed in the case of aromatic alkynes. Moreover, the azide group is sustained up to the final product. The method can be easily adapted for large-scale preparation, and the resulting products can be readily transformed into -difluoro group containing amine and triazole derivatives.

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http://dx.doi.org/10.1021/acs.orglett.9b03593DOI Listing

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