Synthesis of indoles with a polyfluorinated benzene ring

A two-step sequence consisting of a Sonogashira coupling of polyfluorinated 2-iodoanilines with terminal alkynes, followed by a KOH promoted cyclization of the 2-alkynylanilines thus formed, has been developed as a one-pot synthesis of 2-R-indoles (R=n-Bu, Ph, CH2OTHP -> CH2OH, C(CH3)(2)OH -> H) containing a polyfluorinated benzene moiety. (C) 2013 Elsevier Ltd. All rights reserved.