Aminofluorination of 2-alkynylanilines: a Au-catalyzed entry to fluorinated indoles

Beilstein J Org Chem. 2014 Feb 20:10:449-58. doi: 10.3762/bjoc.10.42. eCollection 2014.

Abstract

The scope and limitations of gold-catalyzed tandem cycloisomerization/fluorination reactions of unprotected 2-alkynylanilines to have access to 3,3-difluoro-2-aryl-3H-indoles and 3-fluoro-2-arylindoles are described. An unprecedented aminoauration/oxidation/fluorination cascade reaction of 2-alkynylanilines bearing a linear alkyl group on the terminal triple bond is reported.

Keywords: 2-alkynylanilines; fluorination; gold catalysis; indoles; tandem reactions.