Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles

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. N-Acetylindoles can be...

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Bibliographic Details
Published in:Tetrahedron letters 2008-06, Vol.49 (25), p.4050-4053
Main Authors: Potavathri, Shathaverdhan, Dumas, Ashley S., Dwight, Timothy A., Naumiec, Gregory R., Hammann, Jeffrey M., DeBoef, Brenton
Format: Article
Language:English
Subjects:
Arylation
C–H functionalization
Indole
Oxidative coupling
Palladium
Regioselective
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Summary: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. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.04.073