ortho-Cyanomethylation of aryl fluoroalkyl sulfoxides via a sulfonium-Claisen rearrangement.
Org Biomol Chem
; 22(7): 1495-1499, 2024 Feb 14.
Article
em En
| MEDLINE
| ID: mdl-38293848
ABSTRACT
We hereby report the ortho-cyanomethylation of aryl fluoroalkyl sulfoxides with acetonitrile through a sulfonium-Claisen-type rearrangement. This reaction enables the incorporation of two valuable functional groups, such as the cyanomethyl group and the fluoroalkylthio group, into arenes. Remarkably, fluoroalkylthio groups, such as SCFH2 and SCF2H, bearing active hydrogen, are well tolerated by the reaction. The success of the reaction relies on the use of an excess amount of acetonitrile and the electronegative effect of fluoroalkyl substituents, both of which promote the electrophilic assembly of sulfoxides with acetonitrile. Consequently, the sulfonium-Claisen rearrangement reaction tolerates a wide variety of fluoroalkyl sulfoxides bearing functional groups including halides, nitriles, ketones, sulfones, and amides, which are appealing for subsequent elaboration and exploration.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
China