DOI
10.1021/acs.joc.5c03195
Abstract
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine, 3-alkylated indoles undergo Friedel–Crafts silyloxyalkylation when treated with nonenolizable aldehydes. The reaction is general across a wide range of aromatic aldehydes and tolerates a variety of N-alkylated indoles. Deprotection of the silylated product occurs under standard conditions, and in certain cases the initial TMS-protected product can be isolated in high yield.
Document Type
Article
Publication Date
5-8-2026
Publisher Statement
© 2026 The Authors. Published by American Chemical Society
Open Access - Creative Commons CC BY 4.0
Recommended Citation
Eric Zhou, Helen L. Xia, C. Wade Downey; Friedel–Crafts Addition of 3-Alkylated Indoles to Aldehydes: 2-Hydroxyalkylation Promoted by Trimethylsilyl Trifluoromethanesulfonate. Journal of Organic Chemistry 8 May 2026; 91 (18): 6255–6267. https://doi.org/10.1021/acs.joc.5c03195
