Abstract
N-alkylindoles undergo Friedel–Crafts addition to aryl and secondary alkyl nitrones in the presence of trimethylsilyl trifluoromethanesulfonate and a trialkylamine to produce 3-(1- (silyloxyamino)alkyl)indoles. Spontaneous conversion to the bisindolyl(aryl)methanes, which is thermodynamically favored for nitrones derived from aromatic aldehydes, is suppressed under the reaction conditions. The silyloxyamino group can be deprotected with tetrabutylammonium fluoride to yield the hydroxylamine.
Document Type
Article
Publication Date
2021
Publisher Statement
Copyright © 2021, Journal of Organic Chemistry.
Recommended Citation
Zachary Z. Oracheff, Helen L. Xia, Christopher D. Poff,* Scott E. Isaacson, C. Wade Downey. Friedel–Crafts addition of indoles to nitrones promoted by trimethylsilyl trifluoromethanesulfonate. Journal of Organic Chemistry 2021, 86, 17328-17336.