Photoinduced Copper-Catalyzed Enantioselective Allylic C(sp3)−H Oxidation of Acyclic 1-Aryl-2-alkyl Alkenes as Limiting Substrates

Xuemeng Chen, Heng Hui Li, Søren Kramer*

*Corresponding author for this work

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Abstract

Herein, we disclose a simple copper-catalyzed method for enantioselective allylic C(sp3)−H oxidation of unsymmetrical acyclic alkenes, specifically 1-aryl-2-alkyl alkenes. The C−H substrates are used in limiting amounts, and the products are obtained with high enantioselectivity, E/Z-selectivity, and regioselectivity. The method exhibits broad functional group tolerance, and E/Z-alkene mixtures are suitable C−H substrates. The transformation is enabled by light irradiation, which sustains the enantioselective copper catalysis by photoinduced oxidant homolysis.

Original languageEnglish
Article numbere202413190
JournalAngewandte Chemie - International Edition
Volume63
Issue number47
Number of pages6
ISSN1433-7851
DOIs
Publication statusPublished - 2024

Keywords

  • Copper
  • C−H functionalization
  • Enantioselectivity
  • Oxidation
  • Photocatalysis

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