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Ligand-Promoted Meta-C-H Amination and Alkynylation.
Journal of the American Chemical Society 2016 October 8
Meta-C-H amination and meta-C-H alkynylation using a modified norbornene (methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate) as a transient mediator has been developed for the first time. Both the identification of a mono-protected 3-amino-2-hydroxypyridine/pyridone type ligand and the use of methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate as the mediator are crucial for realizing these two unprecedented meta-C-H transformations. A variety of substrates are compatible with both meta-C-H amination and meta-C-H alkynylation. Amination and alkynylation of heterocyclic substrates including indole, indoline, and indazole afford the desired products in moderate to high yields.
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