Communication

N-Heterocyclic Carbene Catalyzed Reactions of α-Bromo-α,β-unsaturated Aldehydes/α,β-Dibromoaldehydes with 1,3-Dinucleophilic Reagents

  1. Prof. Dr. Changsheng Yao1,*,
  2. Donglin Wang2,
  3. Jun Lu2,
  4. Prof. Dr. Tuanjie Li2,
  5. Weihui Jiao2,
  6. Prof. Chenxia Yu2

Article first published online: 19 JAN 2012

DOI: 10.1002/chem.201103358

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 7, pages 1914–1917, February 13, 2012

Additional Information

How to Cite

Yao, C., Wang, D., Lu, J., Li, T., Jiao, W. and Yu, C. (2012), N-Heterocyclic Carbene Catalyzed Reactions of α-Bromo-α,β-unsaturated Aldehydes/α,β-Dibromoaldehydes with 1,3-Dinucleophilic Reagents. Chem. Eur. J., 18: 1914–1917. doi: 10.1002/chem.201103358

Author Information

  1. 1

    School of Chemistry and Engineering, Key Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou, Jiangsu 221116 (P.R. China), Fax: (+86) 516-83500365

  2. 2

    School of Chemistry and Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou Jiangsu 221116 (P.R. China)

*School of Chemistry and Engineering, Key Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou, Jiangsu 221116 (P.R. China), Fax: (+86) 516-83500365

Publication History

  1. Issue published online: 3 FEB 2012
  2. Article first published online: 19 JAN 2012
  3. Manuscript Received: 25 OCT 2011

Funded by

  • Priority Academic Program Development of Jiangsu Higher Education Institutions
  • Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions. Grant Number: 09KJA430003
  • Natural Science Foundation of Xuzhou City. Grant Number: XM09B016

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Keywords:

  • carbenes;
  • heterocycles;
  • N-heterocyclic carbenes;
  • redox chemistry;
  • umpolung
Thumbnail image of graphical abstract

Carbenes ring true: N-Heterocyclic carbene (NHC) catalyzed reactions of α-bromo-α,β-unsaturated aldehydes/α,β-dibromoaldehydes with 1,3-dinucleophilic reagents, such as 1,3-dicarbonyl compounds, β-enamino ketones, and β-enamino esters through umpolung processes gave functionalized 3,4-dihydropyranones and 3,4-dihydropyridinones (see scheme). The availability of the starting materials, lack of external oxidant, and usefulness of the products make this strategy attractive.

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