title: Friedel-Crafts Hydroxyalkylation of Indoles Mediated by Trimethylsilyl Trifluoromethanesulfonate.
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.
authors.affiliation: University of Richmond , Gottwald Center for the Sciences, 28 Westhampton Way, Richmond, Virginia 23173, United States.
authors.forename: C Wade
authors.initials: CW
authors.lastname: Downey
authors.affiliation: University of Richmond , Gottwald Center for the Sciences, 28 Westhampton Way, Richmond, Virginia 23173, United States.
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Poff
authors.affiliation: University of Richmond , Gottwald Center for the Sciences, 28 Westhampton Way, Richmond, Virginia 23173, United States.
authors.forename: Alissa N
authors.initials: AN
authors.lastname: Nizinski
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013816:Thermodynamics; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007211:Indoles; D008698:Mesylates; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate