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Organic carbonates as alternative solvents for asymmetric hydrogenation
Author(s) -
Schäffner Benjamin,
Andrushko Vasyl,
Bayardon Jerome,
Holz Jens,
Börner Armin
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20720
Subject(s) - chemistry , acetonitrile , propylene carbonate , cationic polymerization , asymmetric hydrogenation , chirality (physics) , carbonate , catalysis , phosphine , organic chemistry , enantioselective synthesis , electrochemistry , chiral symmetry breaking , quantum mechanics , quark , nambu–jona lasinio model , physics , electrode
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. Chirality 2009. © 2009 Wiley‐Liss, Inc.