A serendipitous C-C bond formation reaction between michael donors and diiminoquinoid ring assisted by quaternary ammonium fluoride

Abstract

An efficient C-C bond formation reaction assisted by a fluoride ion has been Identified for N,N'-diphenyl-1,4-phenylenediimine with the compounds having an active methylene group. The reaction follows the typical Michael addition fashion and proceeds to completion within 1 h at 70 °C in acetonitrile in the presence of tetrabutylammonlum fluoride (TBAF), while the same reaction failed to proceed in the absence of a fluoride anion. The new finding reported herein also offers an unprecedented method for a direct functionallzation of polyaniline backbone with versatile functional alkyl groups © 2009 American Chemical Society.