N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)(2) as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective arylation at indole's 2-position.
Indole derivatives R 0140Oxidant-Controlled Regioselectivity in the Oxidative Arylation of N-Acetylindoles. -The Pd-catalyzed coupling of N-substituted indoles with benzene or pentafluorobenzene gives 2-arylated derivatives when AgOAc is used as the oxidant. Reaction with Cu(OAc)2 afford the 3-arylated products. -(POTAVATHRI, S.; DUMAS, A. S.; DWIGHT, T. A.; NAUMIEC, G. R.; HAMMANN, J. M.; DEBOEF*, B.; Tetrahedron Lett. 49 (2008) 25, 4050-4053; Dep. Chem., Univ. R. I., Kingston, RI 02881, USA; Eng.) -Mais 41-114
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