FeCl3-mediated friedel-crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines

Abstract

IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl3 features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.