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

• Published in: Journal of organic chemistry Vol. 78; no. 2; pp. 419 - 426
• Main Authors: Beattie, Christopher, North, Michael, Villuendas, Pedro, Young, Carl
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 18.01.2013
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo302317w

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.