Preparation of 4-Allylisoindoline via a Kumada Coupling with Allylmagnesium Chloride

A practical, cost-effective Kumada coupling for the preparation of 4-allylisoindoline has been developed. The first catalyst screen for this reaction with allylmagnesium reagents is described. The challenges associated with product isomerization have been minimized by a thorough understanding of the reaction parameters. Additionally, a novel workup protocol has been developed to render Mg salts soluble in aqueous media at pH 10.