Abstract
Radical fluorination has been known for a long time, but synthetic applications were severely limited by the hazardous nature of the first generation of reagents such as F-2 and the strongly electrophilic nature of the second generation of reagents such as N-fluorobenzenesulfonimide (NFSI) and Selecfluor (R). Here, we report the preparation, use and properties of N-fluoro-N- arylsulfonamides (NFASs), a class of fluorinating reagents suitable for radical fluorination under mild conditions. Their N-F bond dissociation energies (BDE) are 30-45 kJ moI(-1) lower than the N-F BDE of the reagents of the second generation. This favors clean radical fluorination processes over undesired side reactions. The utility of NFASs is demonstrated by a metal-free radical hydrofluorination of alkenes including an efficient remote C-H fluorination via a 1,5-hydrogen atom transfer. NFASs have the potential to become the reagents of choice in many radical fluorination processes.
Dokumententyp: | Zeitschriftenartikel |
---|---|
Fakultät: | Chemie und Pharmazie > Department Chemie |
Themengebiete: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
URN: | urn:nbn:de:bvb:19-epub-67345-2 |
ISSN: | 2041-1723 |
Sprache: | Englisch |
Dokumenten ID: | 67345 |
Datum der Veröffentlichung auf Open Access LMU: | 19. Jul. 2019, 12:22 |
Letzte Änderungen: | 04. Nov. 2020, 13:49 |