Elsevier

Tetrahedron Letters

Volume 65, 16 February 2021, 152749
Tetrahedron Letters

Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile

https://doi.org/10.1016/j.tetlet.2020.152749Get rights and content

Highlights

  • An efficient and simple method on the construction of aryl cyanides has been developed.

  • Different from most known strategies, no additive was needed in this reaction.

  • N,N-Dimethylaminomalononitrile was used as the cyanide source with moderate toxicity and better stability.

Abstract

A copper-promoted cyanation of aryl iodides has been successfully developed by using N,N-dimethyl aminomalononitrile as the cyanide source with moderate toxicity and better stability. This reaction features broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.

Section snippets

Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgments

This work is supported by the National Natural Science Foundation of China (21472077 and 21772071), the Fundamental Research Funds for the Central Universities (lzujbky-2018-134), the Science and Technology Program of Gansu Province (20JR10RA608), and Department of Education of Guangdong Province (No. 2017KTSCX185, 2017KSYS010, 2016KCXTD005, 2019KZDXM035).

References (28)

  • T. Schareina et al.

    Chem. Commun.

    (2004)
    H. Jiang et al.

    Catal. Lett.

    (2013)
    B. Karimi et al.

    ChemCatChem

    (2015)
    M. Nasrollahzadeh et al.

    J. Colloid Interface Sci.

    (2016)
    V. Kandathil et al.

    Catal. Lett.

    (2018)
    S. Sobhani et al.

    Org. Process Res. Dev.

    (2019)
    M. Nasrollahzadeh et al.

    Appl. Organomet. Chem.

    (2019)
    S. Hemmati et al.

    Appl. Organomet. Chem.

    (2019)
  • L.R. Mills et al.

    J. Am. Chem. Soc.

    (2019)
  • (a) C. Qi, X. Hu and H. He, Synlett, 2016, 27, 1979-1982; (b) C. Qi, X. Hu and H. Jiang, Chem. Commun., 2017, 53,...
  • B.-H. Zhang, L.-S. Lei, S.-Z. Liu, X.-Q. Mou, W.-T. Liu, S.-H. Wang, J. Wang, W. Bao and K. Zhang, Chem. Commun., 2017,...
  • L.-S. Lei et al.

    Adv. Synth. Catal.

    (2020)
  • (a) H.-P. Husson, J. Royer, Chem. Soc. Rev., 1999, 28, 383. (b) D. Enders, J. P. Shilvock, Chem. Soc. Rev., 2000, 29,...
  • F.F. Fleming

    Nat. Prod. Rep.

    (1999)
    J.S. Miller et al.

    Acc. Chem. Res.

    (2001)
    F.F. Fleming et al.

    Chem. Rev.

    (2003)
    F.F. Fleming et al.

    J. Med. Chem.

    (2010)
  • P. Anbarasan et al.

    Chem. Soc. Rev.

    (2011)
  • (a) A. Pongratz, Monats Chem, 1927, 48, 585-591; (b) K. Takagi, T. Okamoto, Y. Sakakibara and S. Oka, Chem. Lett.,...
  • C. Yang et al.

    Org. Lett.

    (2004)
    Y.J. Shim et al.

    J. Organomet. Chem.

    (2012)
  • G.P. Ellis et al.

    Chem. Rev.

    (1987)
    D. Wang et al.

    Synlett

    (2008)
  • K. Kim et al.

    Adv. Synth. Catal.

    (2017)
    F.M. Moghaddam et al.

    ChemistrySelect

    (2019)
  • D.M. Tschaen et al.

    Synth. Commun.

    (1994)
    M. Alterman et al.

    J. Org. Chem.

    (2000)
    L. Zhao et al.

    J. Org. Chem.

    (2020)
  • A. Muhammad Siddique et al.

    Tetrahedron

    (2020)
  • Cited by (0)

    Patent pending, Chinese patent application (No. 202011088148.7).

    View full text