One-Pot Gold-Catalyzed Aminofluorination of Unprotected 2-Alkynylanilines
- 28 May 2013
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 15 (11) , 2766-2769
Abstract
A tandem gold(I)-catalyzed aminocylization/fluorination and a two-step, one-pot gold(III)-catalyzed cyclization/electrophilic fluorination provide a convenient and general method for the synthesis of 3,3-difluoro-2-substituted-3H-indoles in good yield under mild conditions. Extension of the procedure to the synthesis of 2-aryl-3-fluoro-1H-indoles is described. The reaction proceeds smoothly in green ethanol and does not require any base, acid, or N-protective group.Keywords
This publication has 76 references indexed in Scilit:
- C(sp3)–F reductive elimination from alkylgold(iii) fluoride complexesChemical Science, 2011
- Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocyclesBeilstein Journal of Organic Chemistry, 2011
- One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilinesBeilstein Journal of Organic Chemistry, 2011
- Bystanding F+ Oxidants Enable Selective Reductive Elimination from High‐Valent Metal Centers in CatalysisAngewandte Chemie International Edition, 2011
- Gold-Catalyzed Oxidative Coupling Reactions with AryltrimethylsilanesOrganic Letters, 2010
- Gold‐Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive EliminationAngewandte Chemie International Edition, 2010
- Gold-Catalyzed Three-Component Coupling: Oxidative Oxyarylation of AlkenesJournal of the American Chemical Society, 2010
- Serendipitous Discovery of the Catalytic Hydroammoniumation and Methylamination of AlkynesAngewandte Chemie International Edition, 2010
- Synthetic studies of 3-(3-fluorooxindol-3-yl)-l-alanineJournal of Fluorine Chemistry, 2008
- Fluorinated nucleosides: Synthesis and biological implicationJournal of Fluorine Chemistry, 2008