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Regioselective C-H Alkylation via Carboxylate-Directed Hydroarylation in Water
Guodong Zhang1, Fan Jia1, Lukas J Gooßen1
1Evonic Chair of Organic Chemistry, Ruhr-Universität Bochum, Universitätsstr. 150, 44801, Bochum, Germany.
Abstract:
In the presence of catalytic [RuCl2 (p-cym)]2 and using Li3 PO4 as the base, benzoic acids react with olefins in water to afford the corresponding 2-alkylbenzoic acids in moderate to excellent yields. This C-H alkylation process is generally applicable to diversely substituted electron-rich and electron-deficient benzoic acids, along with α,β-unsaturated olefins including unprotected acrylic acid. The widely available carboxylate directing group can be removed or utilized for further derivatization. Mechanistic investigations revealed that the transformation proceeds via a ruthenacycle intermediate.
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