Molecular Iodine-Catalysed Reductive Alkylation of Indoles: Late-Stage Diversification for Bioactive Molecules

Herein, we report a molecular iodine-catalysed reductive alkylation of indoles with carbonyl compounds using Et3SiH for the efficient synthesis of C3-alkylated indoles. This metal-free and environmental-friendly process exhibits excellent functional group tolerance, mild conditions, and wide substrate scope. Notably, the synthetic usefulness of this strategy to pharmacochemistry was highlighted by the late-stage modification of drug-like molecules.

Automated summary

In this study, a molecular iodine-catalysed reductive alkylation reaction of indoles with carbonyl compounds was reported for the efficient synthesis of C3-alkylated indoles. This metal-free and environmentally friendly process showed excellent functional group tolerance, mild reaction conditions, and a wide range of substrates. Importantly, the synthetic usefulness of this strategy in pharmacology was demonstrated through the late-stage modification of drug-like molecules.