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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


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Volume 91, Issue 10

Issues

Electrochemical synthesis and amidation of benzoin: benzamides from benzaldehydes

Daniele Rocco
  • Dipartimento di Scienze di Base e Applicate per l’Ingegneria (SBAI), Sapienza University of Rome, via del Castro Laurenziano, 7, 00161 Rome, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Isabella Chiarotto
  • Dipartimento di Scienze di Base e Applicate per l’Ingegneria (SBAI), Sapienza University of Rome, via del Castro Laurenziano, 7, 00161 Rome, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Leonardo Mattiello
  • Dipartimento di Scienze di Base e Applicate per l’Ingegneria (SBAI), Sapienza University of Rome, via del Castro Laurenziano, 7, 00161 Rome, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Fabiana Pandolfi
  • Dipartimento di Scienze di Base e Applicate per l’Ingegneria (SBAI), Sapienza University of Rome, via del Castro Laurenziano, 7, 00161 Rome, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Daniela Zane
  • CNR ISMN Istituto per lo Studio dei Materiali Nanostrutturati, UOS Sapienza, P.le Aldo Moro 5, 00185 Rome, Italy
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  • De Gruyter OnlineGoogle Scholar
/ Marta Feroci
  • Corresponding author
  • Dipartimento di Scienze di Base e Applicate per l’Ingegneria (SBAI), Sapienza University of Rome, via del Castro Laurenziano, 7, 00161 Rome, Italy
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Published Online: 2019-05-31 | DOI: https://doi.org/10.1515/pac-2018-1118

Abstract

The benzoin condensation starting from benzaldehyde and the subsequent benzoin amidation to benzamide can be efficiently carried out under very mild conditions in an electrolysis cell. Among the advantages of using electrochemistry to generate our active reagents, the use of the easily dosed and non pollutant electron, instead of stoichiometric amounts of redox reagents or bases, usually renders the electrochemical methodology “greener” than classical organic reactions. Benzoin is obtained in good yield (85 %) carrying out the reaction in the room temperature ionic liquid BMIm-BF4. In this electrochemical reaction this liquid salt assumes the double role of solvent-supporting electrolyte system and precatalyst, yielding the corresponding N-heterocyclic carbene. The subsequent benzoin amidation is carried out by electrochemically generated superoxide anion, in the presence of an aliphatic primary or secondary amine. In this case the system superoxide/molecular oxygen acts as base and oxidant, yielding very good yields of benzamides (up to 89 %).

Keywords: benzamide; benzoin; electrosynthesis; Eurasia 2018; ionic liquids; N-heterocyclic carbene; superoxide anion

Article note

A collection of invited papers based on presentations at the15th Eurasia Conference on Chemical Sciences (EuAsC2S-15) held at Sapienza University of Rome, Italy, 5–8 September 2018.

References

  • [1]

    H. Lund, O. Hammerich. Organic Electrochemistry. Marcel Dekker Inc., New York (2001).Google Scholar

  • [2]

    D. Kyriacou. Modern Electroorganic Chemistry. Springer-Verlag, Berlin (1994).Google Scholar

  • [3]

    J. Volke, F. Liška. Electrochemistry in Organic Synthesis. Springer-Verlag, Berlin (1994).Google Scholar

  • [4]

    A. Wiebe, T. Gieshoff, S. Möhle, E. Rodrigo, M. Zirbes, S. R. Waldvogel. Angew. Chem. Int. Ed. 57, 5594 (2018).CrossrefGoogle Scholar

  • [5]

    M. Yan, Y. Kawamata, P. S. Baran. Chem. Rev. 117, 13230 (2017).CrossrefGoogle Scholar

  • [6]

    S. Möhle, M. Zirbes, E. Rodrigo, T. Gieshoff, A. Wiebe, S. R. Waldvogel. Angew. Chem. Int. Ed. 57, 6018 (2018).CrossrefGoogle Scholar

  • [7]

    P. Wasserscheid, T. Welton. Ionic Liquids in Synthesis. Wiley VCH, Weinheim (2008).Google Scholar

  • [8]

    M. Feroci, M. Orsini, L. Rossi, A. Inesi. Curr. Org. Synth. 9, 40 (2012).CrossrefGoogle Scholar

  • [9]

    M. Feroci, M. Orsini, A. Inesi. in Green Solvents II. Properties and Applications of Ionic Liquids. A. Mohammad, Inammudin (Eds.), pp. 435–471, Springer, Dordrecht (2012).Google Scholar

  • [10]

    M. Feroci, I. Chiarotto, A. Inesi. Curr. Org. Chem. 17, 204 (2013).Google Scholar

  • [11]

    I. Chiarotto, M. Feroci, G. Sotgiu, A. Inesi. Eur. J. Org. Chem. 2013, 326 (2013).CrossrefGoogle Scholar

  • [12]

    J. R. Dunetz, J. Magano, G. A. Weisenburger. Org. Process Res. Dev. 20, 140 (2016).CrossrefGoogle Scholar

  • [13]

    M. Feroci, I. Chiarotto, A. Inesi. Electrochim. Acta 89, 692 (2013).CrossrefGoogle Scholar

  • [14]

    M. Orsini, I. Chiarotto, M. N. Elinson, G. Sotgiu, A. Inesi. Electrochem. Commun. 11, 1013 (2009).CrossrefGoogle Scholar

  • [15]

    I. Chiarotto, M. Feroci, M. Orsini, M. M. M. Feeney, A. Inesi. Adv. Synth. Catal. 352, 3287 (2010).CrossrefGoogle Scholar

  • [16]

    F. Pandolfi, I. Chiarotto, D. Rocco, M. Feroci. Electrochim. Acta 254, 358 (2017).CrossrefGoogle Scholar

  • [17]

    R. S. Menon, A. T. Biju, V. Nair. Beilstein J. Org. Chem. 12, 444 (2016).CrossrefGoogle Scholar

  • [18]

    M. Feroci, I. Chiarotto, S. Vecchio Ciprioti, A. Inesi. Electrochim. Acta 109, 95 (2013).CrossrefGoogle Scholar

  • [19]

    M. Feroci, I. Chiarotto, A. Inesi. Catalysts 6, 178 (2016).CrossrefGoogle Scholar

  • [20]

    M. Feroci, I. Chiarotto, F. D’Anna, G. Forte, R. Noto, A. Inesi. Electrochim. Acta 153, 122 (2015).CrossrefGoogle Scholar

  • [21]

    M. Feroci, I. Chiarotto, M. Orsini, G. Sotgiu, A. Inesi. Electrochim. Acta 56, 5823 (2011).CrossrefGoogle Scholar

  • [22]

    M. Hayyan, F. S. Mjalli, M. A. Hashim, I. M. AlNashef. J. Mol. Liq. 181, 44 (2013).CrossrefGoogle Scholar

  • [23]

    M. A. Casadei, S. Cesa, F. Micheletti Moracci, A. Inesi, M. Feroci. J. Org. Chem. 61, 380 (1996).CrossrefGoogle Scholar

  • [24]

    M. Singh, R. A. Misra. Synthesis 1989, 403 (1989).CrossrefGoogle Scholar

About the article

Published Online: 2019-05-31

Published in Print: 2019-10-25


Citation Information: Pure and Applied Chemistry, Volume 91, Issue 10, Pages 1709–1715, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2018-1118.

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