CuH-Catalyzed Regio- and Stereoselective Hydroalkoxylation of Styrenes with Acetal-Based Peroxides

An oxygen-umpolung-enabled, copper-catalyzed hydroalkoxylation reaction of styrenes has been developed. The key to success lies with the CF3-substituted electron-deficient acetal-based peroxides, which enables the chemo-, regio-, and stereoselective net hydroalkoxylation of alkene π-bonds under the initiation by CuH species. The use of a chiral bisphosphine ligand further enables the delivery of enantioenriched chiral ethers with good enantiomeric ratios.

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Publication Details

Journal
ACS Catalysis
Published
2025-05-05
DOI
https://doi.org/10.1021/acscatal.5c02202
Citations
4
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
2.15

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article

CuH-Catalyzed Regio- and Stereoselective Hydroalkoxylation of Styrenes with Acetal-Based Peroxides

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4 citations
ACS Catalysis
Asymmetric Hydrogenation and Catalysis
2.15
article

CuH-Catalyzed Regio- and Stereoselective Hydroalkoxylation of Styrenes with Acetal-Based Peroxides

Kosuke Yasui, Koji Hirano, Kyosuke Fujiwara, Yuki Kojima, Shōgo Nakamura
article en
4 citations

Abstract

An oxygen-umpolung-enabled, copper-catalyzed hydroalkoxylation reaction of styrenes has been developed. The key to success lies with the CF3-substituted electron-deficient acetal-based peroxides, which enables the chemo-, regio-, and stereoselective net hydroalkoxylation of alkene π-bonds under the initiation by CuH species. The use of a chiral bisphosphine ligand further enables the delivery of enantioenriched chiral ethers with good enantiomeric ratios.

ACS CatalysisVol. 15(10)
Center for Research and Interdisciplinarity (FR), Graduate School USA (US), The University of Osaka (JP)
Japan Society for the Promotion of Science, Fusion Oriented REsearch for disruptive Science and Technology
Clean water and sanitation
Openalex Percentile: Top 13%
Asymmetric Hydrogenation and Catalysis
2.15
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