Elsevier

Tetrahedron Letters

Volume 55, Issue 7, 12 February 2014, Pages 1373-1375
Tetrahedron Letters

AgF/TFA-promoted highly efficient synthesis of α-haloketones from haloalkynes

https://doi.org/10.1016/j.tetlet.2014.01.027Get rights and content

Abstract

A AgF/TFA-promoted highly efficient synthesis of a wide range of α-haloketones from haloalkynes is described. The reactions are conducted under convenient conditions and provide products in moderate to excellent yields, with broad substrate scope, including a variety of aromatic chloroalkynes and bromoalkynes.

Graphical abstract

A AgF/TFA-promoted highly efficient synthesis of a wide range of α-haloketones from haloalkynes is described. The reactions are conducted under convenient conditions and provide products in moderate to excellent yields, with broad substrate scope, including a variety of aromatic chloroalkynes and bromoalkynes.

  1. Download : Download full-size image

Section snippets

Acknowledgements

The authors thank the NSFC (21202023 and 21162001), NSF of Jiangxi Province (20114BAB213006) for financial support.

References and notes (23)

  • K.M. Brummond et al.

    Tetrahedron Lett.

    (1999)
  • E.M. Kosower et al.

    J. Org. Chem.

    (1963)
  • A. Podgorsek et al.

    J. Org. Chem.

    (2009)
    Z. Xu et al.

    Synth. Commun.

    (2006)
    J.C. Lee et al.

    Synth. Commun.

    (2006)
    J.G. Lee et al.

    Bull. Korean Chem. Soc.

    (1995)
    A. Guy et al.

    Synthesis

    (1982)
  • A.W. Erian et al.

    Molecules

    (2003)
  • N. De Kimpe et al.
  • J.G. Aston et al.

    Org. Synth. Coll. III

    (1955)
  • D.P. Wyman et al.

    J. Org. Chem.

    (1964)
  • J.C. Lee et al.

    Bull. Korean Chem. Soc.

    (2003)
    T.A. Salama et al.

    Tetrahedron Lett.

    (2011)
    I. Pravst et al.

    Tetrahedron

    (2008)
  • D.P. Curran et al.

    J. Org. Chem.

    (1989)
    S. Karimi et al.

    J. Org. Chem.

    (1995)
    O.A. Attanasi et al.

    Org. Lett.

    (2006)
    H.Y. Choi et al.

    Org. Lett.

    (2003)
    P.L. Julian et al.

    J. Am. Chem. Soc.

    (1950)
  • L.C. King et al.

    J. Org. Chem.

    (1964)
    X. Shi et al.

    J. Org. Chem.

    (1993)
  • Cited by (39)

    • A green and recyclable CuSO<inf>4</inf>·5H<inf>2</inf>O/ionic liquid catalytic system for the CO<inf>2</inf>-promoted hydration of propargyl alcohols: an efficient assembly of α-hydroxy ketones

      2022, Journal of Catalysis
      Citation Excerpt :

      However, the employment of toxic mercury and corrosive acid blocked its further applications in modern green and sustainable society. Over the past several decades, alternative systems containing Cu [12–14], Ag [15–20], Zn [21–23], Au [24–40], Fe [41–43], Co [44–47], Ru [48–50], Pd [51–53], Pt [54], In [55,56], Sn [57,58], Hf [59]salts, etc. have been established and remarkable progress has been achieved for the conversion of most alkynes. However, for a series of specific alkynes that contain hydroxyl groups, namely propargyl alcohols, seldom systems were reported to show general and excellent catalytic activity.

    View all citing articles on Scopus
    View full text