Manganese(I) Catalyzed ortho C−H Allylation of Benzoic Acids |
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Authors: | Jonas F Goebel Johanna Stemmer Florian Belitz Lukas J Gooßen |
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Institution: | Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany |
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Abstract: | The 3d-metal catalyst Mn(CO)5Br was found to efficiently promote ortho C−H allylations of arenecarboxylates in the presence of neocuproine as the ligand. Despite the simplicity of directing group and catalyst system, the selectivity goes well beyond the state-of-the-art in that mono-allylated products are obtained exclusively with high selectivities for the least hindered ortho-position. The directing group can optionally be removed by in situ decarboxylation, opening up a regioselective entry to allyl arenes. The preparative utility of the process and its othogonality to other approaches was demonstrated by 44 products with otherwise hard-to-access substitution patterns, including 3-bromo-allylbenzene, 3-allylbenzofuran, or 5-allyl-2-methylnitrobenzene. |
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Keywords: | Allylation C−H Activation Carboxylic Acids Manganese |
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