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

Herein, we disclose a simple copper-catalyzed method for enantioselective allylic C(sp<sup>3</sup>)-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 International Edition
Published
2024-08-12
DOI
https://doi.org/10.1002/anie.202413190
Citations
18
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
4.50

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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
18 citations
Angewandte Chemie International Edition
Catalytic C–H Functionalization Methods
4.50
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
18 citations

Abstract

Herein, we disclose a simple copper-catalyzed method for enantioselective allylic C(sp<sup>3</sup>)-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 Chemie International EditionVol. 63(47)
Technical University of Denmark (DK)
Danmarks Frie Forskningsfond, Novo Nordisk Fonden
Openalex Percentile: Top 5%
Catalytic C–H Functionalization Methods
4.50
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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 International Edition (2024) | TGRS Research Map | TGRS