Communication

Synthesis of Acrylonitriles through an FeCl3-Catalyzed Domino Propargylic Substitution/Aza-Meyer–Schuster Rearrangement Sequence

  1. Lu Hao1,
  2. Feng Wu2,
  3. Zong-Cang Ding1,
  4. Su-Xia Xu1,
  5. Yan-Li Ma1,
  6. Prof. Dr. Li Chen1,
  7. Prof. Dr. Zhuang-Ping Zhan1,2,*

Article first published online: 24 APR 2012

DOI: 10.1002/chem.201200763

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 21, pages 6453–6456, May 21, 2012

Additional Information

How to Cite

Hao, L., Wu, F., Ding, Z.-C., Xu, S.-X., Ma, Y.-L., Chen, L. and Zhan, Z.-P. (2012), Synthesis of Acrylonitriles through an FeCl3-Catalyzed Domino Propargylic Substitution/Aza-Meyer–Schuster Rearrangement Sequence. Chem. Eur. J., 18: 6453–6456. doi: 10.1002/chem.201200763

Author Information

  1. 1

    Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318

  2. 2

    School of Pharmaceutical Sciences, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318

*Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318

Publication History

  1. Issue published online: 15 MAY 2012
  2. Article first published online: 24 APR 2012
  3. Manuscript Received: 7 MAR 2012

Funded by

  • NSFC. Grant Number: 21072159
  • 973 Projects. Grant Number: 2011CB935901
  • NFFTBS. Grant Number: J1030415
  • Science & Technology Bureau of Xiamen
  • 3502Z20093007

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Keywords:

  • acrylonitriles;
  • cyanides;
  • domino reactions;
  • iron;
  • propargylic substitution;
  • rearrangement
Thumbnail image of graphical abstract

Nontoxic cyanide source: An unprecedented route to acrylonitriles by employing propargylic alcohols and para-tolylsulfonohydrazide as a combined cyano source has been developed (see scheme). This efficient and practical cyanation reaction proceeds through an FeCl3-catalyzed domino propargylic substitution/aza-Meyer–Schuster rearrangement sequence, the rearrangement process of which is reported for the first time.

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