Photoinduced Decarboxylative Radical Coupling Reaction of Multiply Oxygenated Structures by Catalysis of Pt-Doped TiO2.
J Org Chem
; 87(1): 730-736, 2022 Jan 07.
Article
en En
| MEDLINE
| ID: mdl-34936365
ABSTRACT
A new reaction system was devised for decarboxylative radical coupling reactions by heterogeneous semiconductor photoredox catalysis. When an α-alkoxy carboxylic acid and Pt-doped TiO2 in EtOAc were irradiated with a violet light-emitting diode at room temperature, the photogenerated electron hole of TiO2 oxidatively induced the ejection of CO2 via the formation of a carboxyl radical to produce the corresponding α-alkoxy radical. C(sp3)-C(sp3) bond formation between the radicals led to dimers with reductive conversion of protons to H2 by the photogenerated electron. Alternatively, in the presence of an electron-deficient olefin, an intermolecular radical addition reaction occurred, resulting in the formation of a 1,4-adduct via single-electron reduction and subsequent protonation. These operationally simple and mild transformations are amenable to the one-step assembly of densely oxygenated linear and branched carbon chains.
Texto completo:
1
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2022
Tipo del documento:
Article
País de afiliación:
Japón