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 substra...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2022; no. 34
Main Authors Cheng, Xionglve, Wang, Lili, Liu, Yide, Wan, Xiao, Xiang, Zixin, Li, Ruyi, Wan, Xiaobing
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 13.09.2022
Subjects
Alkylation
Carbonyl compounds
Carbonyls
Functional groups
Indoles
Iodine
Metal-free
Reduction
Reductive alkylation
Silanes
Substrates
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Summary: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. A molecular iodine‐catalysed efficient synthesis of C3‐alkylated indoles was well established, which exhibits excellent functional group tolerance, mild conditions, and wide substrate scope. Notably, this environmental‐friendly methodology also finds application in the late‐stage modification of drug‐like molecules.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200502