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

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...

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Bibliographic Details
Published inOrganic letters Vol. 11; no. 24; pp. 5586 - 5589
Main Authors Paike, Vijaykumar V, Balakumar, R, Chen, Hsin-Yu, Shih, Hong-Pin, Han, Chien-Chung
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.12.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONCURRENT REDUCTION
AZA-HENRY REACTION
CATALYSIS
PYRROLIDINE
ACID
ADDITIONS
FACILE
BASE
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol9025843