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J Org Chem. 2015 Oct 16;80(20):10364-9. doi: 10.1021/acs.joc.5b01681. Epub 2015 Sep 29.

Friedel-Crafts Hydroxyalkylation of Indoles Mediated by Trimethylsilyl Trifluoromethanesulfonate.

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1
University of Richmond , Gottwald Center for the Sciences, 28 Westhampton Way, Richmond, Virginia 23173, United States.

Abstract

Indoles and N-alkylindoles undergo Friedel-Crafts addition to aldehydes in the presence of trimethylsilyl trifluoromethanesulfonate and a trialkylamine to produce 3-(1-silyloxyalkyl)indoles. Neutralization of the reaction mixture with pyridine followed by deprotection under basic conditions with tetrabutylammonium fluoride provides the 1:1 adduct as the free alcohol. This method prevents spontaneous conversion of the desired products to the thermodynamically favored bisindolyl(aryl)methanes, a process typically observed when indoles are reacted with aldehydes under acidic conditions.

PMID:
26393376
DOI:
10.1021/acs.joc.5b01681
[Indexed for MEDLINE]

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