Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication.
Angew Chem Int Ed Engl
; 58(38): 13318-13322, 2019 09 16.
Article
em En
| MEDLINE
| ID: mdl-31306561
ABSTRACT
Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33â
V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C-H/N-H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Transporte de Elétrons
/
Radicais Livres
Limite:
Humans
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article