Rhodium (III) Catalyzed Regioselective and Enantiospecific Allylic Arylation in Water by bêta-Fluorine Elimination of the Allylic Fluo-ride: toward the Synthesis of Z-alkenyl-unsaturated amides - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2020

Rhodium (III) Catalyzed Regioselective and Enantiospecific Allylic Arylation in Water by bêta-Fluorine Elimination of the Allylic Fluo-ride: toward the Synthesis of Z-alkenyl-unsaturated amides

Résumé

A direct coupling of arylboronic acids with allylic fluorides was carried out in water without additives using a rhodium(III) catalyst (Cp*RhCl2)2. The transformation proceeded with excellent γ-selectivity to afford major allyl–aryl coupling products (Z) γ-substituted α,β-unsaturated amides. The reactions of α-chiral allylic fluorides took place with excellent α-to-γ chirality transfer to give allylated arenes with a stereogenic center at the benzylic and allylic position.

Domaines

Chimie
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Dates et versions

hal-03085464 , version 1 (21-12-2020)

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Citer

Clément Casalta, Samir Bouzbouz. Rhodium (III) Catalyzed Regioselective and Enantiospecific Allylic Arylation in Water by bêta-Fluorine Elimination of the Allylic Fluo-ride: toward the Synthesis of Z-alkenyl-unsaturated amides. Organic Letters, 2020, 22 (6), pp.2359-2364. ⟨10.1021/acs.orglett.0c00551⟩. ⟨hal-03085464⟩
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