Asymmetric, Remote C(sp3)-H Arylation via Sulfinyl-Smiles Rearrangement.
Angew Chem Int Ed Engl
; 63(17): e202319158, 2024 Apr 22.
Article
en En
| MEDLINE
| ID: mdl-38506603
ABSTRACT
An efficient asymmetric remote arylation of C(sp3)-H bonds under photoredox conditions is described here. The reaction features the addition radicals to a double bond followed by a site-selective radical translocation (1,n-hydrogen atom transfer) as well as a stereocontrolled aryl migration via sulfinyl-Smiles rearrangement furnishing a wide range of chiral α-arylated amides with up to >99 1â
er. Mechanistic studies indicate that the sulfinamide group governs the stereochemistry of the product with the aryl migration being the rate determining step preceded by a kinetically favored 1,n-HAT process.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2024
Tipo del documento:
Article
País de afiliación:
Suiza