Two-in-One Role of Benzophenone in Photoinduced C(sp3)-H Monofluoralkenylation: Hydrogen-Atom Transfer and Single-Electron Transfer.
J Org Chem
; 89(11): 8272-8285, 2024 Jun 07.
Article
en En
| MEDLINE
| ID: mdl-38775941
ABSTRACT
A new protocol for monofluoralkenylation of C(sp3)-H bonds with gem-difluoroalkenes was reported. In this protocol, benzophenone serves as a photocatalyst with dual roles of hydrogen-atom transfer and single-electron transfer. The excited state of benzophenone abstracts a hydrogen atom from a C(sp3)-H bond to generate a corresponding carbon radical, which subsequently undergoes a radical addition/SET/ß-F elimination process rather than radical-radical cross-coupling of previous work. This reaction shows high regioselectivity for the α-carbon atoms of ethers, thioethers, and amines, enabling the preparation of monofluoroalkenes.
Texto completo:
1
Banco de datos:
MEDLINE
Idioma:
En
Año:
2024
Tipo del documento:
Article