Regioselective Introduction of Indolin-3-one Moieties to Substituted Heteroaromatic Compounds
Andrew J Daszczynski1, Nina Bui1, F G West1
1Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
None:
C2-substituted indolin-3-ones are formed via a mild dual catalytic method involving the generation of a reactive C-acylimine species that can be intercepted by a variety of nucleophilic arenes. The transient C-acylimine electrophile could be trapped regioselectively by a variety of arenes, on which the most reactive site was blocked, offering a new scope of products. Competition experiments show that the C-acylimine electrophile exhibits selectivity for pyrrole over other heteroaromatic traps. Indolin-3-one functionalization of melatonin, protected amino acids, and dipeptides showcases the potential of this chemistry for late-stage diversification of biomolecules containing electron-rich arene units.
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