Navigation auf zora.uzh.ch

Search ZORA

ZORA (Zurich Open Repository and Archive)

Asymmetric, Remote C(sp$^3$)−H Arylation via Sulfinyl‐Smiles Rearrangement

Hu, Yawen; Hervieu, Cédric; Merino, Estíbaliz; Nevado, Cristina (2024). Asymmetric, Remote C(sp$^3$)−H Arylation via Sulfinyl‐Smiles Rearrangement. Angewandte Chemie Internationale Edition, 63(17):e202319158.

Abstract

An efficient asymmetric remote arylation of C(sp$^{3}$)−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.

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Language:English
Date:22 April 2024
Deposited On:25 Oct 2024 09:56
Last Modified:26 Oct 2024 20:00
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1002/anie.202319158
PubMed ID:38506603
Project Information:
  • Funder: NCCR Catalysis
  • Grant ID:
  • Project Title:
  • Funder: China Scholarship Council
  • Grant ID:
  • Project Title:
Download PDF  'Asymmetric, Remote C(sp$^3$)−H Arylation via Sulfinyl‐Smiles Rearrangement'.
Preview
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)

Metadata Export

Statistics

Citations

Dimensions.ai Metrics

Altmetrics

Downloads

1 download since deposited on 25 Oct 2024
1 download since 12 months
Detailed statistics

Authors, Affiliations, Collaborations

Similar Publications