Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation-Defluorination Pathway.

Org Lett

Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.

Published: April 2020

A one-pot approach to fluorinated hydroxamic acid, amide, and thioamide derivatives is reported. The reaction proceeds via an N-perfluoroalkylation of nitrosoarenes with perfluoroalkanesulfinates, resulting in labile N-perfluoroalkylated hydroxylamines. By the addition of suitable additives, a controllable oxy/thiodefluorination of the fluorinated hydroxylamine intermediates was achieved. The method highlights N-perfluoroalkylated amines as versatile intermediates for further synthesis.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7311088PMC
http://dx.doi.org/10.1021/acs.orglett.0c00768DOI Listing

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