Ferrocene based chiral binuclear η6-benzene-Ru(II)-phosphinite complexes: Synthesis, characterization and catalytic activity in asymmetric reduction of ketones

被引:8
作者
Al-bayati, Yaser W. Abdlhmed [1 ]
Karakas, Duygu Elma [1 ,2 ]
Meric, Nermin [1 ]
Aydemir, Murat [1 ]
Durap, Feyyaz [1 ]
Baysal, Akin [1 ]
机构
[1] Dicle Univ, Fac Sci, Dept Chem, TR-21280 Diyarbakir, Turkey
[2] Siirt Univ, Sci & Technol Applicat & Res Ctr SIUBTAM, Siirt, Turkey
关键词
asymmetric transfer hydrogenation; catalysis; chiral; phosphinite; ruthenium; TRANSFER HYDROGENATION; AROMATIC KETONES; PHOSPHINITE LIGANDS; RUTHENIUM(II) COMPLEXES; ACETOPHENONE; DERIVATIVES; BEARING; SYSTEM;
D O I
10.1002/aoc.3919
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In the present study, a series of chiral C-2-symmetric ferrocenyl based binuclear (6)-benzene-Ru(II) complexes bearing diphenylphosphinite and diisopropylphosphinite moieties have been synthesised. The new binuclear (6)-benzene-Ru(II)-phosphinite complexes were characterised based on nuclear magnetic resonance (H-1, C-13, P-31-NMR), FT-IR spectroscopy and elemental analysis. Then, these complexes have been screened as catalytic precursors in the transfer hydrogenation of acetophenone with 2-propanol as both the hydrogen source and solvent in the presence of KOH. The corresponding optically active secondary alcohols were obtained in excellent conversion rates between 96 and 99% and moderate to good enantioselectivities (up to 78% ee). The complex 5 was the most efficient catalyst among the four new complexes investigated herein.
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页数:10
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[1]   Ruthenium(II) complexes derived from C2-symmetric ferrocene-based chiral bis(phosphinite) ligands: synthesis and catalytic activity towards the asymmetric reduction of acetophenones [J].
Ak, B. ;
Durap, F. ;
Aydemir, M. ;
Baysal, A. .
APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (11) :764-770
[2]   Highly efficient iridium catalysts based on C2-symmetric ferrocenyl phosphinite ligands for asymmetric transfer hydrogenations of aromatic ketones [J].
Ak, Bunyamin ;
Aydemir, Murat ;
Durap, Feyyaz ;
Meric, Nermin ;
Elma, Duygu ;
Baysal, Alan .
TETRAHEDRON-ASYMMETRY, 2015, 26 (23) :1307-1313
[3]   The first application of C2-symmetric ferrocenyl phosphinite ligands for rhodium-catalyzed asymmetric transfer hydrogenation of various ketones [J].
Ak, Bunyamin ;
Aydemir, Murat ;
Durap, Feyyaz ;
Meric, Nermin ;
Baysal, Akin .
INORGANICA CHIMICA ACTA, 2015, 438 :42-51
[4]   Readily available ferrocenyl-phosphinite ligands for Ru(II)-catalyzed enantioselective transfer hydrogenation of ketones and fabrication of hybrid heterojunctions [J].
Ak, Bunyamin ;
Aydemir, Murat ;
Ocak, Yusuf Selim ;
Durap, Feyyaz ;
Kayan, Cezmi ;
Baysal, Akin ;
Temel, Hamdi .
INORGANICA CHIMICA ACTA, 2014, 409 :244-253
[5]   Synthesis of epimer of Taniaphos ligand [J].
Almassy, Ambroz ;
Rakovsky, Erik ;
Malastova, Andrea ;
Soradova, Zuzana ;
Sebesta, Radovan .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 805 :130-138
[6]   Novel pyrazolylphosphite- and pyrazolylphosphinite-ruthenium(II) complexes as catalysts for hydrogenation of acetophenone [J].
Amenuvor, Gershon ;
Obuah, Collins ;
Nordlander, Ebbe ;
Darkwa, James .
DALTON TRANSACTIONS, 2016, 45 (34) :13514-13524
[7]   Ionic liquid based Ru(II)-phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol [J].
Aydemir, Murat ;
Rafikova, Khadichakhan ;
Kystaubayeva, Nurzhamal ;
Pasa, Salih ;
Meric, Nermin ;
Ocak, Yusuf Selim ;
Zazybin, Alexey ;
Temel, Hamdi ;
Gurbuz, Nevin ;
Ozdemir, Ismail .
POLYHEDRON, 2014, 81 :245-255
[8]   Bis(phosphinite) with C2-Symmetric Axis; Effects on the Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Acetophenone Derivatives [J].
Aydemir, Murat ;
Durap, Feyyaz ;
Kayan, Cezmi ;
Baysal, Akin ;
Turgut, Yilmaz .
SYNLETT, 2012, (19) :2777-2784
[9]   trans- and cis-Ru(II) aminophosphine complexes: Syntheses, X-ray structures and catalytic activity in transfer hydrogenation of acetophenone derivatives [J].
Aydemir, Murat ;
Baysal, Akin ;
Ozkar, Saim ;
Yildirim, Leyla Tatar .
INORGANICA CHIMICA ACTA, 2011, 367 (01) :166-172
[10]   Asymmetric transfer hydrogenation of aromatic ketones with the ruthenium(II) catalyst derived from C2 symmetric N,N′-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide [J].
Aydemir, Murat ;
Meric, Nermin ;
Durap, Feyyaz ;
Baysal, Akin ;
Togrul, Mahmut .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (09) :1392-1398