Organic carbonates as alternative solvents for asymmetric hydrogenation.
Organic carbonates like propylene carbonate (PC) or butylene carbonate (BC) belong to the class of aprotic, highly dipolar solvents (AHD). Interestingly, their potential as solvents for asymmetric catalysis has been overlooked for a long time. The aim of this work is to evaluate organic carbonates and other organic solvents like THF, CH(2)Cl(2), and acetonitrile as well as members of the AHD-family (DMF, DMSO, etc.) as media for homogeneous asymmetric hydrogenation. For this reason cationic Rh-complexes based on chiral phosphine ligands were tested in the hydrogenation of typical benchmark substrates. In several trials, significant advantages of organic carbonates were found. In contrast to DMSO, DMF and acetonitrile, in PC and BC high conversion rates and excellent enantioselectivities were usually observed.
Schäffner
Benjamin
B
Leibniz-Institut für Katalyse an der Universität Rostock e.V., Rostock 18059, Germany.
Andrushko
Vasyl
V
Bayardon
Jerome
J
Holz
Jens
J
Börner
Armin
A
D002255:Carbonic Acid / Q000737:chemistry*; D002384:Catalysis; D055772:Green Chemistry Technology; D006865:Hydrogenation; D009930:Organic Chemicals / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D009930:Organic Chemicals; D012997:Solvents; D002255:Carbonic Acid; D012238:Rhodium