A Serendipitous C-C Bond Formation Reaction between Michael Donors and Diiminoquinoid Ring Assisted by Quaternary Ammonium Fluoride

作者:Paike Vijaykumar V; Balakumar R; Chen Hsin Yu; Shih Hong Pin; Han Chien Chung*
来源:Organic Letters, 2009, 11(24): 5586-5589.
DOI:10.1021/ol9025843

摘要

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 degrees C in acetonitrile in the presence of tetrabutylammonium 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 functionalization of polyaniline backbone with versatile functional alkyl groups.