Fluoride‐Transfer Asymmetric Allylic Alkylation Enables Regiodivergent, Stereoselective Cross‐Electrophile Coupling
Abstract
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.
Article Details
Authors (6)
Jordi Duran
Section of Organic Chemistry Department of Inorganic and Organic Chemistry University of Barcelona Carrer Martí i Franquès 1 Barcelona 08028 Spain
Vyali Georgian Moldoveanu
Section of Organic Chemistry Department of Inorganic and Organic Chemistry University of Barcelona Carrer Martí i Franquès 1 Barcelona 08028 Spain
Claudia Barroso
Section of Organic Chemistry Department of Inorganic and Organic Chemistry University of Barcelona Carrer Martí i Franquès 1 Barcelona 08028 Spain
Geraldo Augusto Pereira
Section of Organic Chemistry Department of Inorganic and Organic Chemistry University of Barcelona Carrer Martí i Franquès 1 Barcelona 08028 Spain
Bart Limburg
Section of Organic Chemistry Department of Inorganic and Organic Chemistry University of Barcelona Carrer Martí i Franquès 1 Barcelona 08028 Spain
Xavier Companyó
Section of Organic Chemistry Department of Inorganic and Organic Chemistry University of Barcelona Carrer Martí i Franquès 1 Barcelona 08028 Spain