Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols.
Org Lett
; 23(15): 5761-5765, 2021 08 06.
Article
em En
| MEDLINE
| ID: mdl-34292755
ABSTRACT
A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2021
Tipo de documento:
Article