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- Title
Asymmetric, Remote C(sp<sup>3</sup>)−H Arylation via Sulfinyl‐Smiles Rearrangement.
- Authors
Hu, Yawen; Hervieu, Cédric; Merino, Estíbaliz; Nevado, Cristina
- 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 : 1 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.
- Subjects
ARYLATION; DOUBLE bonds; STEREOCHEMISTRY; RADICALS (Chemistry); ABSTRACTION reactions; ASYMMETRIC synthesis
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 17, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202319158