Bifunctional One‐Component Catalysts for the Addition of Carbon Dioxide to Epoxides. Issue 3 (9th December 2014)

• Record Type: Journal Article
• Authors: Büttner, Hendrik; Lau, Kornelia; Spannenberg, Anke; Werner, Thomas
• Is Part Of: ChemCatChem. Volume 7:Issue 3(2015:Feb.)
• Page Start: 459
• Page End: 467
• Publication Date: 2014-12-09
• Subjects: Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201402816
• Languages: English
• ISSNs: 1867-3880

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Several bifunctional ammonium salts were synthesized and employed as one‐component catalysts for the conversion of CO₂ and epoxides to produce cyclic carbonates. These catalysts show superior activities compared to their monofunctional analogs. A turnover number of up to 693 and a turnover frequency of up 392 h⁻¹ could be achieved for the best catalyst. Moreover, the effect of various solvents has been studied. All employed solvents and the product formed had a negative influence on substrate conversion. The scope and limitation of the reaction has been studied carefully for two general reaction protocols at 45 and 90 °C. In over 20 examples, the isolated yields after filtration were 90 %. In addition, we present the first organocatalyzed synthesis of a cyclohexene‐based naturally occurring cyclic carbonate, and its molecular structure was determined by XRD. Furthermore, we demonstrate that the reaction can be performed even on a multigram scale and can be monitored by in situ FTIR spectroscopy.</p> </abstract>