Approach Toward Stereoselective α‐Arylation by Pd/Cu‐Catalyzed Arylboration of Electron Deficient Alkenes

Palladium-catalyzed cross coupling of enolates-α-arylation-is an established method for chemical synthesis. A major challenge in the field is control of stereochemistry for the α-carbon. This is typically due to facile epimerization under the basic reaction conditions for α-arylation. In this study, an alternative approach is presented that involves the Pd/Cu-catalyzed arylboration of electron deficient alkenes. The products are generated with high levels of diastereoselectivity for a broad range of substitution patterns. Enantioselective variants are also presented in addition to product derivatizations.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-03-27
DOI
https://doi.org/10.1002/anie.202424073
Citations
5
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
4.68

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article

Approach Toward Stereoselective α‐Arylation by Pd/Cu‐Catalyzed Arylboration of Electron Deficient Alkenes

M. Kevin Brown, A. Pearson, Stanna K. Dorn, Michael Reilly et al.
5 citations
Angewandte Chemie International Edition
Catalytic Cross-Coupling Reactions
4.68
article

Approach Toward Stereoselective α‐Arylation by Pd/Cu‐Catalyzed Arylboration of Electron Deficient Alkenes

M. Kevin Brown, A. Pearson, Stanna K. Dorn, Michael Reilly, Suman Das
article en
5 citations

Abstract

Palladium-catalyzed cross coupling of enolates-α-arylation-is an established method for chemical synthesis. A major challenge in the field is control of stereochemistry for the α-carbon. This is typically due to facile epimerization under the basic reaction conditions for α-arylation. In this study, an alternative approach is presented that involves the Pd/Cu-catalyzed arylboration of electron deficient alkenes. The products are generated with high levels of diastereoselectivity for a broad range of substitution patterns. Enantioselective variants are also presented in addition to product derivatizations.

Angewandte Chemie International EditionVol. 64(22)
Indiana University Bloomington (US)
National Institutes of Health
Openalex Percentile: Top 6%
Catalytic Cross-Coupling Reactions
4.68
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