Fluoride‐Transfer Asymmetric Allylic Alkylation Enables Regiodivergent, Stereoselective Cross‐Electrophile Coupling

Asymmetric allylic alkylation (AAA) is a widely used strategy for stereoselective formation of C─C bonds. Yet, conventional methods often exhibit poor atom economy as the leaving group is generally wasted. Herein, we report a fluoride-transfer asymmetric allylic alkylation (AAA) in which all the atoms of the reagents are incorporated into the final products. The catalytic platform enables regiodivergent, stereoselective cross-electrophile coupling of allyl fluorides and gem-difluoroalkenes, where the regiochemical outcome is directed by the selective catalytic activation of one or the other electrophilic partner. The resulting atom-efficient AAA protocol provides a regiocontrollable access to homoallylic trifluoromethylated compounds from a common set of electrophilic starting materials.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-11-22
DOI
https://doi.org/10.1002/anie.202520513
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Fluoride‐Transfer Asymmetric Allylic Alkylation Enables Regiodivergent, Stereoselective Cross‐Electrophile Coupling

Vyali Georgian Moldoveanu, Xavier Companyó, Bart Limburg, Jordi Duran et al.
Angewandte Chemie International Edition
Fluorine in Organic Chemistry
article

Fluoride‐Transfer Asymmetric Allylic Alkylation Enables Regiodivergent, Stereoselective Cross‐Electrophile Coupling

Vyali Georgian Moldoveanu, Xavier Companyó, Bart Limburg, Jordi Duran, Gislaine Ribeiro Pereira, Claudia Barroso
article en

Abstract

Asymmetric allylic alkylation (AAA) is a widely used strategy for stereoselective formation of C─C bonds. Yet, conventional methods often exhibit poor atom economy as the leaving group is generally wasted. Herein, we report a fluoride-transfer asymmetric allylic alkylation (AAA) in which all the atoms of the reagents are incorporated into the final products. The catalytic platform enables regiodivergent, stereoselective cross-electrophile coupling of allyl fluorides and gem-difluoroalkenes, where the regiochemical outcome is directed by the selective catalytic activation of one or the other electrophilic partner. The resulting atom-efficient AAA protocol provides a regiocontrollable access to homoallylic trifluoromethylated compounds from a common set of electrophilic starting materials.

Angewandte Chemie International EditionVol. 65(2)
i2CAT (ES), Universitat de Barcelona (ES)
European Commission, Generalitat de Catalunya, Universität Wien, Universitat de Barcelona, Agència de Gestió d'Ajuts Universitaris i de Recerca, Agencia Estatal de Investigación
Openalex Percentile: Top 71%
Fluorine in Organic Chemistry
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