Dearomatization of aryl sulfoxides: a switch between mono- and dual-difluoroalkylation.
Chem Sci
; 11(11): 3048-3053, 2020 Feb 25.
Article
de En
| MEDLINE
| ID: mdl-34122809
ABSTRACT
Herein we describe the dearomatization of aryl sulfoxides with difluoroenol silyl ether (DFESE) using a rearrangement/addition protocol. The selection of the sulfoxide activator determines whether one or two difluoroalkyl groups are incorporated into dearomatized products. Using TFAA can deliberately halt the reaction at the mono-difluoroalkylated dearomatized intermediate formed via a [3,3]-rearrangement, which can be further trapped by external nucleophiles to give mono-difluoroalkylated alicycles. In contrast, switching to Tf2O enhances the electrophilicity of dearomatized intermediates, thus allowing for the adoption of a second DFESE to produce dual-difluoroalkylated alicycles.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Langue:
En
Journal:
Chem Sci
Année:
2020
Type de document:
Article