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Rhodium(III) Catalyzed Regioselective and Stereospecific Allylic Arylation in Water by β-Fluorine Elimination of the Allylic Fluoride: Toward the Synthesis of Z-Alkenyl-Unsaturated Amides

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02508863
Contributor : Madeleine Roux-Merlin <>
Submitted on : Monday, March 16, 2020 - 10:24:39 AM
Last modification on : Thursday, July 2, 2020 - 3:29:51 AM

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Clément Casalta, Samir Bouzbouz. Rhodium(III) Catalyzed Regioselective and Stereospecific Allylic Arylation in Water by β-Fluorine Elimination of the Allylic Fluoride: Toward the Synthesis of Z-Alkenyl-Unsaturated Amides. Organic Letters, American Chemical Society, 2020, 22 (6), pp.2359-2364. ⟨10.1021/acs.orglett.0c00551⟩. ⟨hal-02508863⟩

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