期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 62, 期 24, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202301839
关键词
Allylation; C-H Activation; Carboxylic Acids; Manganese
The 3d-metal catalyst Mn(CO)(5)Br efficiently promotes ortho C-H allylations of arenecarboxylates in the presence of neocuproine as the ligand. The selectivity of this relatively simple directing group and catalyst system surpasses the state-of-the-art, exclusively producing mono-allylated products with high selectivities for the least hindered ortho-position. The directing group can be selectively removed by in situ decarboxylation, providing a regioselective access to allyl arenes. The preparative utility of this process and its orthogonality to other approaches were demonstrated by the synthesis of 44 products with otherwise difficult substitution patterns.
The 3d-metal catalyst Mn(CO)(5)Br 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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