Synthesis and Characterization of Imidazolium Chiral Ionic Liquids Prepared from Low-Cost Chiral Amines for Its Use in Asymmetric Organic Electrosynthesis

Tuesday, May 13, 2014: 17:40
Floridian Ballroom D, Lobby Level (Hilton Orlando Bonnet Creek)
B. A. Frontana-Uribe (Centro Conjunto de Investigación en Química Sustentable UAEMéx-UNAM, Universidad Nacional Autónoma de México) and E. Rodríguez-Cárdenas (Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM)
Room temperature ionic liquids (RTIL’s) are organic salts with low melting points (less than 0°C) and are in the focus of green chemists as alternative solvents, due to their attractive properties such as chemical electrochemical and thermal stability, non-flammability, low vapor pressure, high ionic conductivity and designable structure.[1],[2] These solvents are constituted of organic cations and inorganic or organic anions. So there is a great possibility to design and tune their properties for various applications just by careful selection of the cation or anion to obtain the desired properties.[3],[4]  In the last few years, researchers have turned their interest to synthesis of chiral ionic liquids (CILs). Many CILs have been designed, synthesized and used in organic reactions.[5] Nevertheless, the use of RTIL’s in organic electrosynthesis is well known,[6] the use of the CILs has been overlooked. Chiral imidazolium ionic liquids derived from both enantiomers of a-phenylethylamine using a simple and low cost methodology were synthesized. In this communication it is reported their physicochemical properties, thermal behavior, water content and hydrophilicity, density and electrochemical behaviour. The first studies of the application of these chiral solvents in organic electrosynthesis will be discussed, using the classical pinacolic coupling and CO2activation looking for asymmetric electrochemical reactions.

The authors thank the financial support of PAPIIT-UNAM project IN202011.

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[4] Davis, J. H. Chem. Lett. 2004, 33, 1072–1077.

[5] a)Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumont, A.-C.; Plaquevent, J.-C. Tetrahedron Asymmetry 2003, 14, 3081–3093. b) Ding, J.; Armstrong, D.W. Chirality 2005, 17, 281–292. c)Baudequin, C.; Brégeon, D.; Levillain, J.; Guillen, F.; Plaquevent, J.-C.; Gaumont, A.-C. Tetrahedron Asymmetry 2005, 16, 3921–3945.

[6] Bornemann, S., Handy, S.T. Molecules 2011, 16, 5963-5974.