One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

Abstract

The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents).

Keywords

• alkynylation
• direct functionalization
• gold
• hypervalent iodine
• indoles