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

Autor:	Pedro Villuendas, Carl Young, Christopher Beattie, Michael North
Rok vydání:	2013
Předmět:	Organic Chemistry Inorganic chemistry Epoxide Catalysis Metal Hydroxylation chemistry.chemical_compound chemistry Reagent visual_art Carbon dioxide visual_art.visual_art_medium Bimetallic strip Bar (unit)
Zdroj:	The Journal of Organic Chemistry. 78:419-426
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo302317w
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d5cfe72d67f57ff00de0a927d19d7eb4 https://doi.org/10.1021/jo302317w Zobrazit plný text záznamu