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Carbocation/Polyol Systems as Efficient Organic Catalysts for the Preparation of Cyclic Carbonates

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Author(s)

  • Yuri A. Rulev
  • Zalina T. Gugkaeva
  • Anastasia V. Lokutova
  • Victor I. Maleev
  • Alexander S. Peregudov
  • Xiao Wu
  • Michael North
  • Yuri N. Belokon

Department/unit(s)

Publication details

JournalCHEMSUSCHEM
DateAccepted/In press - 16 Nov 2016
DateE-pub ahead of print (current) - 16 Nov 2016
Early online date16/11/16
Original languageEnglish

Abstract

Carbocation/polyol systems are shown to be highly efficient catalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide at 50°C and 5MPa CO2 pressure. The best activity was shown by the combination of crystal violet and 1,1'-bi-2-naphthol (BINOL), which could be recycled five times with no loss of activity. The presence of specific interactions between the amino groups of the carbocation and the hydroxyl protons was confirmed by NMR experiments. The Job plots for the crystal violet iodide/BINOL and brilliant green iodide/BINOL systems showed that the catalytic systems consist of one molecule of the carbocation and one molecule of BINOL. Mechanistic studies using a deuterated epoxide indicate that there was some loss of epoxide stereochemistry during the reaction, but predominant retention of stereochemistry is observed. On this basis, a catalytic cycle is proposed.

Bibliographical note

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

    Research areas

  • Carbocations, Carbon dioxide, Catalysts, Cyclic carbonates, Phenols

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