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

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journal contribution
posted on 17.12.2009, 00:00 by Vijaykumar V. Paike, R. Balakumar, Hsin-Yu Chen, Hong-Pin Shih, Chien-Chung Han
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 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.