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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

Lookup NU author(s): Christopher Beattie, Professor Michael North, Dr Pedro Villuendas, Dr Carl Young

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Abstract

The effect of moderate temperatures (22-100 degrees 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.

Publication metadata

Author(s): Beattie C, North M, Villuendas P, Young C

Publication type: Article

Publication status: Published

Journal: Journal of Organic Chemistry

Year: 2013

Volume: 78

Issue: 2

Pages: 419-426

Print publication date: 21/12/2012

ISSN (print): 0022-3263

ISSN (electronic): 1520-6904

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/jo302317w

DOI: 10.1021/jo302317w

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