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

Shathaverdhan Potavathri, University of Rhode Island
Ashley S. Dumas, University of Rhode Island
Timothy A. Dwight, University of Rhode Island
Gregory R. Naumiec, University of Rhode Island
Jeffrey M. Hammann, University of Rhode Island
Brenton DeBoef, University of Rhode Island

Abstract

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. © 2008 Elsevier Ltd. All rights reserved.