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

Organic Letters
Vijaykumar V PaikeChien-Chung Han

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 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.

References

Mar 18, 2004·Journal of the American Chemical Society·Benjamin M NugentJeffrey N Johnston
Dec 30, 2004·Angewandte Chemie·Tehshik P Yoon, Eric N Jacobsen
Sep 24, 2005·Organic Letters·José Luis García RuanoM Belén Cid
Sep 28, 2006·Journal of the American Chemical Society·Jian WangWei Wang
Oct 13, 2006·Organic & Biomolecular Chemistry·Chien-Chung HanMing-Tsu Chung
Apr 19, 2007·Organic Letters·Barry M Trost, David W Lupton
Nov 30, 2007·The Journal of Organic Chemistry·Hui ZhouXiaoming Feng
Feb 6, 2008·Journal of the American Chemical Society·Magno Agostinho, Shū Kobayashi
May 31, 2008·Journal of the American Chemical Society·Enrique Gomez-BengoaClaudio Palomo

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