Regioselective Synthetic Approach to Higher Alkenes from Lower Alkenes with Sulfoxides in the Fe3+/H2O2 System via Direct Alkylation or Arylation of the Csp2-H Bond on the CâC Bond of Alkenes.
J Org Chem
; 87(11): 7022-7032, 2022 Jun 03.
Article
em En
| MEDLINE
| ID: mdl-35583475
ABSTRACT
The regioselective synthetic approach to higher alkenes from lower alkenes by using sulfoxides as alkyl or aryl reagents in the Fe3+/H2O2 system has been developed. This reaction realized direct alkylation or arylation of alkenes. In this reaction, sulfoxides afforded one Csp3 or Csp2 atom to the CâC bond of alkenes; one new Csp2-Csp3 bond or Csp2-Csp2 bond was formed. Nearly 40 products including di-, tri-, and tetra-substituted products were regioselectively synthesized. Both aliphatic and aromatic alkenes could participate in this reaction. Moreover, not only dimethyl sulfoxide but also three other sulfoxides can be applied to this reaction, including diethyl, dibenzyl, and diphenyl sulfoxide. The mechanism studies showed that this reaction may experience a coupling process via radical addition-elimination and the Fe3+/H2O2 system made the sulfoxides offered one alkyl or aryl radical to the CâC bond of alkenes.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
China