Efficient Guanidine-Catalyzed Alkylation of Indoles with Fluoromethyl Ketones in the presence of Water
- 13 April 2009
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (10), 2093-2096
- https://doi.org/10.1021/ol9005079
Abstract
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.Keywords
This publication has 30 references indexed in Scilit:
- Catalytic Asymmetric Friedel−Crafts Alkylation Reactions—Copper Showed the WayChemical Reviews, 2008
- Asymmetric Friedel–Crafts Alkylation of Indoles with Methyl (E)-2-Oxo-4-aryl-3-butenoates Catalyzed by Sc(OTf)3/pyboxChemistry – A European Journal, 2008
- Triflic Acid-Catalyzed Highly Stereoselective Friedel−Crafts Aminoalkylation of Indoles and PyrrolesOrganic Letters, 2008
- Strategies for nucleophilic, electrophilic, and radical trifluoromethylationsJournal of Fluorine Chemistry, 2007
- Highly Enantioselective Synthesis of Tetrahydro-β-Carbolines and Tetrahydro-γ-Carbolines Via Pd-Catalyzed Intramolecular Allylic AlkylationJournal of the American Chemical Society, 2006
- Photoinduced 1,4-Additions of Indoles to EnonesThe Journal of Organic Chemistry, 2005
- Synthesis of N-Heteroaryl(trifluoromethyl)hydroxyalkanoic Acid Esters by Highly Efficient Solid Acid-Catalyzed Hydroxyalkylation of Indoles and Pyrroles with Activated Trifluoromethyl KetonesAdvanced Synthesis & Catalysis, 2005
- Fast reactions ‘on water’Nature, 2005
- A Journey Across Recent Advances in Catalytic and Stereoselective Alkylation of IndolesSynlett, 2005
- New Catalytic Approaches in the Stereoselective Friedel–Crafts Alkylation ReactionAngewandte Chemie-International Edition, 2004