Ionic liquid-mediated benzoyl transfer-coupling in the Suzuki and Sonogashira reactions and aryl transfer-coupling by decarbonylative Heck reaction, using N-Benzoyl-saccharin (NBSac) as reagent

https://doi.org/10.1016/j.tetlet.2020.151987Get rights and content

Highlights

  • Facile access to diverse libraries of diarylketones, keto-ethynes and diaryl-ethenes.

  • N-Benzoylsaccharin for transfer-benzoylation in Suzuki and Sonogashira reactions.

  • N-Benzoylsaccharin for decarbonylative arylation in Heck coupling.

  • Catalysis by either Pd or Ni.

  • [BMIM][X] as solvent, [PAIM][NTf2] as base, guanidinium-IL as acidic/basic IL.

  • Potential for recycling/reuse of the IL solvent.

Abstract

The efficacy of N-benzoyl-saccharin (NBSac) as reagent for selective benzoyl transfer-coupling in the Suzuki reaction in BMIM-IL/[PAIM][NTf2] as solvent/base, and in the Sonogashira reaction employing guanidinium-IL (GIL) as solvent, are demonstrated. Decarbonylative aryl transfer-coupling occurs in the Heck reaction employing GIL as solvent. The reactions are catalyzed by Pd(OAc)2 or NiCl2(dppp), are performed under mild conditions in good yields, and have the potential for recycling/reuse of the IL solvent. Collectively, these methods provide facile access to diverse libraries of diarylketones, keto-ethynes and diaryl-ethenes.

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

Authors at Karnatak University thank the University Scientific and Instrument Center, KUD for IR, 1H and 13C NMR, and the NMR Research Centre at Indian Institute of Science Bangalore for 1H and 13C NMR & HRMS Spectra. Financial assistance by VGST-RGS/F/GRD742/2017-18 is gratefully acknowledged. KKL thanks University of North Florida for the outstanding faculty scholarship and presidential professorship awards, as well as Dean’s Research Council and UNF Foundation Board grants.

References (8)

  • C. Liu et al.

    Org. Lett.

    (2016)
  • C. Liu et al.

    Szostak, M

    J. Org. Chem.

    (2016)
  • R.G. Kalkhambkar et al.

    Tetrahedron Lett.

    (2011)
    G.C. Nandi et al.

    Tetrahedron Lett.

    (2013)
    A.S. Reddy et al.

    Tetrahedron Lett.

    (2015)
    A. Srinivas Reddy et al.

    K

    Tetrahedron Lett.

    (2015)
    H.M. Savanur et al.

    Tetrahedron Lett

    (2016)
    H.M. Savanur et al.

    Appl. Catal. A. Gen.

    (2017)
    H.M. Savanur et al.

    Eur. J. Org. Chem.

    (2018)
    P. Prabhala et al.

    Eur. J. Org. Chem.

    (2019)
    S.M. Sutar et al.

    Eur. J. Org. Chem.

    (2019)
    S.S. Malunavar et al.

    Tetrahedron Lett.

    (2020)
  • L. Lin et al.

    Synlett.

    (2011)
    S. Li et al.

    Organic Lett.

    (2006)
    L.C. Branco et al.

    ACS Catal

    (2011)
    S.S. Chavan et al.

    Catal Lett.

    (2011)
    A. Zhu et al.

    Green Chem.

    (2005)
There are more references available in the full text version of this article.

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