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.