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Amidyl Radicals by Oxidation of α‐Amido‐oxy Acids: Transition‐Metal‐Free Amidofluorination of Unactivated Alkenes
Author(s) -
Jiang Heng,
Studer Armido
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804966
Subject(s) - chemistry , radical , alkene , selectfluor , adduct , ketone , transition metal , aldehyde , fluorine , radical ion , photochemistry , organic chemistry , catalysis , ion
A three‐component transition‐metal‐free amidofluorination of unactivated alkenes and styrenes is presented. α‐Amido‐oxy acids are introduced as efficient and easily accessible amidyl radical precursors that are oxidized by a photoexcited organic sensitizer (Mes‐Acr‐Me) to the corresponding carboxyl radical. Sequential CO 2 and aldehyde/ketone fragmentation leads to an N‐centered radical that adds to an alkene. Commercial Selectfluor is used to trap the adduct radical through fluorine‐atom transfer. The transformation features by high functional‐group tolerance, broad substrate scope, and practical mild conditions. Mechanistic studies support the radical nature of the cascade.