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FeCl3-mediated Friedel-Crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines.

Angewandte Chemie (International ed. in English) (2012-11-06)
Rodolphe Beaud, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent
ABSTRACT

IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3) 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.

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