Rodolphe Beaud, Dr. Régis Guillot, Prof.Dr. Cyrille Kouklovsky and Dr. Guillaume Vincent FeCl3-Mediated Friedel–Crafts Hydroarylation with Electrophilic N-Acetyl Indoles for the Synthesis of Benzofuroindolines Angewandte Chemie International Edition 51
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.
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