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Paike VV, Balakumar R, Chen HY, et al. A serendipitous C-C bond formation reaction between Michael donors and diiminoquinoid ring assisted by quaternary ammonium fluoride. Org Lett. 2009;11(24):5586-9doi: 10.1021/ol9025843.
Paike, V. V., Balakumar, R., Chen, H. Y., Shih, H. P., & Han, C. C. (2009). A serendipitous C-C bond formation reaction between Michael donors and diiminoquinoid ring assisted by quaternary ammonium fluoride. Organic letters, 11(24), 5586-9. https://doi.org/10.1021/ol9025843
Paike, Vijaykumar V, et al. "A serendipitous C-C bond formation reaction between Michael donors and diiminoquinoid ring assisted by quaternary ammonium fluoride." Organic letters vol. 11,24 (2009): 5586-9. doi: https://doi.org/10.1021/ol9025843
Paike VV, Balakumar R, Chen HY, Shih HP, Han CC. A serendipitous C-C bond formation reaction between Michael donors and diiminoquinoid ring assisted by quaternary ammonium fluoride. Org Lett. 2009 Dec 17;11(24):5586-9. doi: 10.1021/ol9025843. PMID: 19928999.
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Org Lett. 2009 Dec 17;11(24):5586-9. doi: 10.1021/ol9025843.

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

Organic letters

Vijaykumar V Paike, R Balakumar, Hsin-Yu Chen, Hong-Pin Shih, Chien-Chung Han

Affiliations

  1. Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, ROC.

PMID: 19928999 DOI: 10.1021/ol9025843

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.

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