Photoinduced Copper‐Catalyzed Enantioselective Allylic C(sp<sup>3</sup>)−H Oxidation of Acyclic 1‐Aryl‐2‐alkyl Alkenes as Limiting Substrates

Abstract Herein, we disclose a simple copper‐catalyzed method for enantioselective allylic C(sp 3 )−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.

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Publication Details

Journal
Angewandte Chemie
Published
2024-08-12
DOI
https://doi.org/10.1002/ange.202413190
Citations
1
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
0.25

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article

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

Heng‐Hui Li, Søren Kramer, Xuemeng Chen
1 citations
Angewandte Chemie
Oxidative Organic Chemistry Reactions
0.25
article

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

Heng‐Hui Li, Søren Kramer, Xuemeng Chen
article en
1 citations

Abstract

Abstract Herein, we disclose a simple copper‐catalyzed method for enantioselective allylic C(sp 3 )−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.

Angewandte ChemieVol. 136(47)
Technical University of Denmark (DK)
Novo Nordisk, Danmarks Frie Forskningsfond, Novo Nordisk Fonden
Openalex Percentile: Top 49%
Oxidative Organic Chemistry Reactions
0.25
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Photoinduced Copper‐Catalyzed Enantioselective Allylic C(sp<sup>3</sup>)−H Oxidation of Acyclic 1‐Aryl‐2‐alkyl Alkenes as Limiting Substrates — Heng‐Hui Li, Søren Kramer, et al. · Angewandte Chemie (2024) | TGRS Research Map | TGRS