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Amidyl Radicals by Oxidation of α‐Amido‐oxy Acids: Transition‐Metal‐Free Amidofluorination of Unactivated Alkenes
- Source :
- Angewandte Chemie. 130:10867-10871
- Publication Year :
- 2018
- Publisher :
- Wiley, 2018.
-
Abstract
- 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 CO2 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.
- Subjects :
- chemistry.chemical_classification
Ketone
Alkene
010405 organic chemistry
Radical
Substrate (chemistry)
General Chemistry
General Medicine
Photochemistry
010402 general chemistry
Aldehyde
01 natural sciences
Catalysis
Adduct
0104 chemical sciences
chemistry.chemical_compound
chemistry
Transition metal
Selectfluor
Subjects
Details
- ISSN :
- 15213757 and 00448249
- Volume :
- 130
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie
- Accession number :
- edsair.doi.dedup.....8d2329b51ca4f2a183f1c9141a5dbe33