Regiospecific ortho-C−H Allylation of Benzoic Acids
A. Stefania Trita
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorAgostino Biafora
FB Chemie-Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663 Kaiserslautern, Germany
Search for more papers by this authorDr. Martin Pichette Drapeau
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorPhilip Weber
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Lukas J. Gooßen
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorA. Stefania Trita
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorAgostino Biafora
FB Chemie-Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663 Kaiserslautern, Germany
Search for more papers by this authorDr. Martin Pichette Drapeau
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorPhilip Weber
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Lukas J. Gooßen
Fakultät Chemie und Biochemie, Ruhr Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany
Search for more papers by this authorAbstract
A carboxylate-directed ortho-C−H functionalization has been developed and it allows the regiospecific introduction of allyl residues to benzoic acids. In the presence of a [Ru(p-cymene)Cl2]2 and K3PO4, benzoic acids react with allyl acetates at only 50 °C to give the corresponding ortho-allylbenzoic acids. The protocol is generally applicable to both electron-rich and electron-poor benzoic acids in combination with linear and branched allyl acetates. The products can be further functionalized in situ, for example, by double-bond migration, lactonization, or decarboxylation.
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