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Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalysed by Aluminium Heteroscorpionate Complexes

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JournalChemCatChem
DateAccepted/In press - 5 May 2016
DatePublished (current) - 30 May 2016
Issue number12
Volume8
Number of pages9
Pages (from-to)2100–2108
Original languageEnglish

Abstract

The combination of an aluminium(heteroscorpionate) complex and tetrabutylammonium bromide acts as a highly efficient catalyst system for the synthesis of oxazolidinones from epoxides and isocyanates. Twenty two complexes were tested derived from a range of bispyrazole ligands and containing 1-3 aluminium atoms per complex. The optimal catalyst was found to be a bimetallic complex of a thioacetamidate ligand. Under the optimal reaction conditions (80°C in toluene for 24h using 5mol% of both aluminium catalyst and tetrabutylammonium bromide co-catalyst), six epoxides were reacted with six aromatic isocyanates, giving 25 oxazolidinones in moderate to excellent yields showing broad substrate scope. The regiochemistry of the reaction (to produce 3,4- or 3,5-oxazolidinones) is controlled by the substrate with epoxide ring opening occurring preferentially at the less hindered end of the epoxide unless a substituent on the epoxide can stabilise a positive charge.

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© Wiley 2016. 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

  • Aluminium, Heterocycles, Homogeneous catalysis, Ligand effects, Regioselectivity

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