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Influence of Temperature and Pressure on Cyclic Carbonate Synthesis Catalyzed by Bimetallic Aluminum Complexes and Application to Overall syn-Bis-hydroxylation of Alkenes

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    Influence of Temperature and Pressure on Cyclic Carbonate Synthesis Catalyzed by Bimetallic Aluminum Complexes and Application to Overall syn-Bis-hydroxylation of Alkenes
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    School of Chemistry and University Research Centre in Catalysis and Intensified Processing, Newcastle University, Bedson Building, Newcastle upon Tyne, NE1 7RU, England, U.K.
    *E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2013, 78, 2, 419–426
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    https://doi.org/10.1021/jo302317w
    Published December 21, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    The effect of moderate temperatures (22–100 °C) and pressures (1–10 bar) on the synthesis of cyclic carbonates from epoxides and carbon dioxide catalyzed by a combination of bimetallic aluminum complexes and tetrabutylammonium bromide is investigated. The combined bimetallic complex and tetrabutylammonium bromide catalyst system is shown to be an order of magnitude more active than the use of tetrabutylammonium bromide alone at all temperatures and pressures studied. At the higher temperatures and pressures used, disubstituted epoxides become substrates for the reaction and it is shown that reactions proceed with retention of the epoxide stereochemistry. This allowed a route for the overall syn-bis-hydroxylation of alkenes to be developed without the use of hazardous metal based reagents. At higher pressures it is also possible to use compressed air as the carbon dioxide source.

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    1H and 13C NMR and GCMS spectra for cyclic carbonates; 1H and 13C NMR spectra for epoxides 5a–e and diols 7a–d. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Org. Chem. 2013, 78, 2, 419–426
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