Ruthenium-Catalyzed C–H Functionalization of Benzoic Acids with Allyl Alcohols: A Controlled Reactivity Switch between C–H Alkenylation and C–H Alkylation Pathways

A highly selective and switchable ruthenium-catalyzed ortho C–H alkylation and C–H alkenylation of benzoic acids with allyl alcohols is reported. A complete switch in selectivity is achieved upon tuning the reactivity of the organometallic intermediate in the carboxylate-directed C–H activation to provide access to highly useful motifs such as 2-alkylbenzoic acids and phthalides.