A regioselective direct carboxamidation reaction of 2-indolylmethanols
with readily available isocyanoesters/isocyanides has been reported
in this work. The reaction was catalyzed by Bronsted acid such as p-TsOH to deliver the benzylic regioselective amides in
67–86% yield under mild conditions. The developed methodology
provides alternative access to traditional metal-free carboxamidation
via C–C and C–O bond formation with high atom economy.
Furthermore, the developed approach was diversified to synthesize
chiral indole-2-carboxamide derivatives with a moderate enantiomeric
excess (61–73% ee) using an (R)-chiral phosphoric acid.
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