Efficient guanidine-catalyzed alkylation of indoles with fluoromethyl ketones in the presence of water.
A simple and efficient guanidine-catalyzed methodology for the direct preparation of trifluoromethyl-indolyl-phenylethanols in the presence of water is reported. This synthetically viable class of compounds is obtained in excellent yields (up to 98%) through Friedel-Crafts-type alkylation of indoles with aromatic fluoromethyl ketones. Exceptional reaction scope of indoles and alkylating agents is described.
Dipartimento di Chimica G. Ciamician, via Selmi 2, 40126 Bologna, Italy. marco.bandini@unibo.it
Marco
M
Bandini
Riccardo
R
Sinisi
D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D019791:Guanidine / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D007659:Ketones; D014867:Water; D019791:Guanidine