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Highly Efficient And Enantioselective Hydrogenation Of Quinolines And Pyridines With Ir-Difluorphos Catalyst.

Weijun Tang, Yawei Sun, Lijin Xu, T. Wang, Qinghua Fan, Kim-hung Lam, A. Chan
Published 2010 · Chemistry, Medicine

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The combination of the readily available chiral bisphosphine ligand Difluorphos with [Ir(COD)Cl](2) in THF resulted in a highly efficient catalyst system for asymmetric hydrogenation of quinolines at quite low catalyst loadings (0.05-0.002 mol%), affording the corresponding products with high enantioselectivities (up to 96%), excellent catalytic activities (TOF up to 3510 h(-1)) and productivities (TON up to 43000). The same catalyst was also successfully applied to the asymmetric hydrogenation of trisubstituted pyridines with nearly quantitative yields and up to 98% ee. In these two reactions, the addition of I(2) additive is indispensable; but the amount of I(2) has a different effect on catalytic performance.
This paper references
10.1021/JA0525298
Catalytic asymmetric hydrogenation of N-iminopyridinium ylides: expedient approach to enantioenriched substituted piperidine derivatives.
C. Legault (2005)
10.1021/AR700094B
Asymmetric hydrogenation of heteroaromatic compounds.
Y. Zhou (2007)
J. Organomet. Chem
S Cho (2007)
10.1021/JA001271C
Catalytic asymmetric hydrogenation of heteroaromatic compounds, indoles [12]
R. Kuwano (2000)
10.1002/ADSC.200390011
Enantioselective Hydrogenation of Imines Using a Diverse Library of Ruthenium Dichloride(diphosphine)(diamine) Precatalysts
Christopher J. Cobley (2003)
10.1021/OL061039X
Ruthenium-catalyzed asymmetric hydrogenation of N-boc-indoles.
R. Kuwano (2006)
10.1002/0471220426
Principles and applications of asymmetric synthesis
Guo‐Qiang Lin (2001)
6 For asymmetric hydrogenation of furans
T Ohta (1995)
10.1021/JO00107A014
Asymmetric Hydrogenation of Olefins with Aprotic Oxygen Functionalities Catalyzed by BINAP-Ru(II) Complexes
T. Ohta (1995)
10.1039/B822822A
Highly enantioselective hydrogenation of quinolines under solvent-free or highly concentrated conditions
Z. Wang (2009)
10.1039/B614446B
Asymmetric hydrogenation of quinolines with high substrate/catalyst ratio.
Wei-jun Tang (2007)
10.1055/s-0029-1218079
pH-Regulated Asymmetric Transfer Hydrogenation of Quinolinesin Water
C. Wang (2009)
Org. Lett. Org. Lett
R Kuwano (2004)
10.1002/ADSC.200505130
Highly Enantioselective Iridium-Catalyzed Hydrogenation of Quinoline Derivatives Using Chiral Phosphinite H8-BINAPO
Kim-hung Lam (2005)
10.1021/ja903547q
Consecutive intramolecular hydroamination/asymmetric transfer hydrogenation under relay catalysis of an achiral gold complex/chiral Brønsted acid binary system.
Z. Han (2009)
10.1021/JA7102422
Catalytic asymmetric hydrogenation of 2,3,5-trisubstituted pyrroles.
R. Kuwano (2008)
10.1016/J.TETASY.2007.04.028
Iridium-catalyzed asymmetric transfer hydrogenation of quinolines with Hantzsch esters
D. Wang (2007)
10.1016/S0022-328X(00)00859-7
Transition metal complexes with the C1-symmetric diphosphines (R)-(R)-3-benzyl-2,4-bis(diphenylphosphino)pentane and (R)-(R)-3-benzyl(p-sulphonate)-2,4-bis(diphenylphosphino)pentane sodium salt. Applications to enantioselective catalysis in different phase systems
C. Bianchini (2001)
Angew. Chem., Int. Ed. J. Am. Chem. Soc
A Wu (2009)
10 For asymmetric transfer hydrogenation of quinolines
K Ito (1001)
10.1016/J.TETLET.2009.11.075
Inhibiting deactivation of iridium catalysts with bulky substituents on coordination atoms
D. Wang (2010)
10.1016/J.TETLET.2008.05.138
Iridium-catalyzed asymmetric hydrogenation of pyridine derivatives, 7,8-dihydro-quinolin-5(6H)-ones
X. Wang (2008)
10.1002/chem.200901477
Unprecedented halide dependence on catalytic asymmetric hydrogenation of 2-aryl- and 2-alkyl-substituted quinolinium salts by using Ir complexes with difluorphos and halide ligands.
Hiroshi Tadaoka (2009)
10.1002/ADSC.200800007
Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of monodentate BINOL-derived phosphoramidites
N. Mrsić (2008)
10.1016/J.JORGANCHEM.2007.06.022
A recyclable palladium-catalyzed modified Friedländer quinoline synthesis
C. S. Cho (2007)
10.1016/S1381-1169(98)00200-3
Enantioselective synthesis of ethyl nipecotinate using cinchona modified heterogeneous catalysts
H.-U. Blaser (1999)
10.1021/CR020049I
New chiral phosphorus ligands for enantioselective hydrogenation.
Wenjun Tang (2003)
5 For asymmetric hydrogenation of quinoxalines
S Murata (1987)
Principles and Applications of Asymmetric Synthesis The Handbook of Homogeneous Hydrogeantion
Chan (2001)
10.1002/ADSC.200800020
Asymmetric Counterion Pair Catalysis: An Enantioselective Brønsted Acid‐Catalyzed Protonation
M. Rueping (2008)
10.1002/anie.200902570
pH-regulated asymmetric transfer hydrogenation of quinolines in water.
C. Wang (2009)
10.1021/OL061681R
Asymmetric homogeneous hydrogenation of 2,5-disubstituted furans.
P. Feiertag (2006)
This journal is © The Royal Society of Chemistry Org. Biomol. Chem
(2010)
Adv. Synth. Catal
H.-U Blaser (2003)
10.1039/B005689H
A one-step, enantioselective reduction of ethyl nicotinate to ethyl nipecotinate using a constrained, chiral, heterogeneous catalyst
S. Raynor (2000)
10.1021/JA0602694
A new class of versatile chiral-bridged atropisomeric diphosphine ligands: remarkably efficient ligand syntheses and their applications in highly enantioselective hydrogenation reactions.
L. Qiu (2006)
3 For recent reviews on asymmetric hydrogenation of heteroaromatic compounds, see: (a) F. Glorius
(1357)
4 For asymmetric hydrogenation of quinolines
W B Wang (1081)
10.1002/ADSC.200800653
Highly Efficient and Versatile Phosphine-Phosphoramidite Ligands for Asymmetric Hydrogenation
Matthias Eggenstein (2009)
Angew. Chem., Int. Ed
M Rueping (2007)
Chem. Rev
Zhang (2003)
10.1039/B602320G
Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphonites.
M. Reetz (2006)
10.1002/ADSC.200404017
Asymmetric Hydrogenation of Quinolines Catalyzed by Iridium with Chiral Ferrocenyloxazoline Derived N,P Ligands
Sheng-mei Lu (2004)
10.1021/jo800779r
Synthesis of tunable bisphosphine ligands and their application in asymmetric hydrogenation of quinolines.
X. Wang (2008)
10.1002/anie.200802237
Hydrogenation of quinolines using a recyclable phosphine-free chiral cationic ruthenium catalyst: enhancement of catalyst stability and selectivity in an ionic liquid.
Haifeng Zhou (2008)
10.1039/B512139F
Asymmetric hydrogenation of aromatic compounds.
F. Glorius (2005)
10.3987/R-1987-03-0763
Hydrogenation and hydrosilylation of quinoxaline by homogeneous rhodium catalysts
S. Murata (1987)
Med. Chem
M Jampilek (2005)
10.1016/J.TETASY.2006.01.016
Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP
R. Kuwano (2006)
10.1002/anie.200703925
The development of double axially chiral phosphoric acids and their catalytic transfer hydrogenation of quinolines.
Qun-Sheng Guo (2008)
10.1021/JA0353762
Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines.
W. Wang (2003)
10.1021/OL0631410
Enantioselective hydrogenation of quinolines catalyzed by Ir(BINAP)-cored dendrimers: dramatic enhancement of catalytic activity.
Z. Wang (2007)
10.1002/ADSC.200390000
Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments
H. Blaser (2003)
10.1002/ANIE.200600191
A highly enantioselective Brønsted acid catalyzed cascade reaction: organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids.
M. Rueping (2006)
10.1021/ol802016w
Air-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives.
Zhiwei Li (2008)
1 For comprehensive reviews
H R Barton (1996)
10.1021/OM980219A
Enantioselective Hydrogenation of 2-Methylquinoxaline to (−)-(2S)-2-Methyl-1,2,3,4-tetrahydroquinoxaline by Iridium Catalysis
C. Bianchini (1998)
10.1021/OL049317K
Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles.
R. Kuwano (2004)
8 For asymmetric hydrogenation of pyridines
S A Raynor (1271)
J. Am. Chem. Soc
R For Asymmetric Hydrogenation Of Pyrroles (2008)
10.1002/ADSC.200900522
Asymmetric Hydrogenation of Quinoxalines Catalyzed by Iridium/PipPhos
Natasa Mrsic (2009)
10.1002/anie.200904518
Asymmetric hydrogenation of quinoxalines with diphosphinite ligands: a practical synthesis of enantioenriched, substituted tetrahydroquinoxalines.
Weijun Tang (2009)
10.1016/S0040-4020(96)00911-8
Recent progress in the synthesis of 1,2,3,4,-tetrahydroquinolines
A. Katritzky (1996)
10.1039/B416397D
Air-stable Ir-(P-Phos) complex for highly enantioselective hydrogenation of quinolines and their immobilization in poly(ethylene glycol) dimethyl ether (DMPEG).
Lijin Xu (2005)
10.1002/ANIE.200701158
Organocatalytic enantioselective reduction of pyridines.
M. Rueping (2007)
10.1016/J.TETASY.2004.02.012
The enantioselective total synthesis of alkaloid (−)-galipeine
P. Yang (2004)
10.1002/ADSC.200800068
Synthesis of Sulfoximine-Derived P,N Ligands and their Applications in Asymmetric Quinoline Hydrogenations
Sheng-Mei Lu (2008)
10.3987/COM-08-S(N)93
IRIDIUM CATALYZED ENANTIOSELECTIVE HYDROGENATION OF N-IMINOPYRIDINIUM YLIDES: MECHANISTIC INSIGHTS
A. Charette (2008)
10.3987/REV-08-SR(N)5
CATALYTIC ASYMMETRIC HYDROGENATION OF 5-MEMBERED HETEROAROMATICS
R. Kuwano (2008)
10.1016/J.TETASY.2007.10.034
Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems
S. Chan (2007)
10.1002/ANIE.200601529
Iridium catalysts with bicyclic pyridine-phosphinite ligands: asymmetric hydrogenation of olefins and furan derivatives.
S. Kaiser (2006)
10.2174/157340605774598108
Quinaldine derivatives: preparation and biological activity.
J. Jampílek (2005)
10.1002/ANIE.200503073
Asymmetric hydrogenation of quinolines and isoquinolines activated by chloroformates.
Sheng-mei Lu (2006)
10.1002/ADSC.200390025
Synthesis and Applications of HexaPHEMP, a Novel Biaryl Diphosphine Ligand
J. P. Henschke (2003)
10.1021/jo900073z
Highly enantioselective iridium-catalyzed hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinolines.
D. Wang (2009)



This paper is referenced by
10.1039/c9cy02147g
Catalysis, kinetics and mechanisms of organo-iridium enantioselective hydrogenation-reduction
Joseph M. Mwansa (2020)
Half-sandwich Complexes of Ruthenium; Synthesis and Application to Catalysis
S. Lee (2014)
10.1002/ADSC.201500491
Versatile (Pentamethylcyclopentadienyl)rhodium‐2,2′‐Bipyridine (Cp*Rh‐bpy) Catalyst for Transfer Hydrogenation of N‐Heterocycles in Water
L. Zhang (2015)
10.1021/ACS.ORGLETT.6B02610
Borane-Catalyzed Transfer Hydrogenations of Pyridines with Ammonia Borane.
Q. Zhou (2016)
10.1007/128_2013_480
Advances in transition metal-catalyzed asymmetric hydrogenation of heteroaromatic compounds.
Y. He (2014)
10.1016/J.TETASY.2015.09.005
Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of quinolines in a sustainable solvent
Ganesh V. More (2015)
10.1016/J.TET.2011.06.067
pH-Regulated transfer hydrogenation of quinoxalines with a Cp*Ir–diamine catalyst in aqueous media
J. Tan (2011)
10.1002/anie.201100008
Ligand-controlled highly regioselective and asymmetric hydrogenation of quinoxalines catalyzed by ruthenium N-heterocyclic carbene complexes.
Slawomir Urban (2011)
10.1016/J.TETLET.2012.06.114
Highly enantioselective hydrogenation of new 2-functionalized quinoline derivatives
Anna M. Maj (2012)
10.1002/ADSC.201300698
Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium‐Catalyzed Asymmetric Hydrogenation in Ionic Liquid
Ziyuan Ding (2013)
10.1007/s11172-012-0326-9
Asymmetric metal complex hydrogenation of 1-methyl-3,4-dihydroisoquinoline in the presence of amidophosphite ligand
S. Lyubimov (2012)
10.1039/c5cc01971k
Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines.
R. Kuwano (2015)
10.1002/ADSC.201000485
Iridium‐Catalyzed Asymmetric Hydrogenation of Quinoline Derivatives with C3*‐TunePhos
Fa-Rong Gou (2010)
10.1002/ANGE.201302218
Ruthenium-NHC-katalysierte asymmetrische Hydrierung von Indolizinen: Zugang zu Indolizidin-Alkaloiden†
Nuria Ortega (2013)
10.1002/anie.201302218
Ruthenium-NHC-catalyzed asymmetric hydrogenation of indolizines: access to indolizidine alkaloids.
N. Ortega (2013)
10.1016/B978-0-08-097742-3.00819-3
8.17 Homogeneous Catalytic Hydrogenation of CåC and CåC
D. Ager (2014)
10.1002/ADSC.201201034
Efficient and Chemoselective Reduction of Pyridines to Tetrahydropyridines and Piperidines via Rhodium-Catalyzed Transfer Hydrogenation
J. Wu (2013)
10.1016/B978-0-08-095167-6.00110-5
1.9 The use of New Phosphines as Powerful Tools in Asymmetric Synthesis of Biologically Active Compounds
C. Busacca (2012)
10.1039/C8GC01025K
Homogeneous catalysed hydrogenation of HMF
Alban Cadu (2018)
10.1039/c3dt51429c
Activation of a (cyclooctadiene) rhodium(I) complex supported by a chiral ferrocenyl phosphine thioether ligand for hydrogenation catalysis: a combined parahydrogen NMR and DFT study.
E. Kozinets (2013)
10.1002/anie.201200963
Brønsted acid activation strategy in transition-metal catalyzed asymmetric hydrogenation of N-unprotected imines, enamines, and N-heteroaromatic compounds.
Z. Yu (2012)
10.1016/J.TETLET.2012.03.036
A new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep and its application in asymmetric hydrogenation
De‐Yang Zhang (2012)
10.1002/9783527691920.CH11
Ir‐Catalyzed Heterocycles Synthesis
Y. Obora (2016)
10.1002/9781118930786.CH3
Oxidation and Reduction
K. K. Banerji (2015)
10.1016/J.CCR.2014.01.023
Enantioselective imine hydrogenation with iridium-catalysts: Reactions, mechanisms and stereocontrol
K. Hopmann (2014)
10.3390/molecules24030401
HMPA-Catalyzed Transfer Hydrogenation of 3-Carbonyl Pyridines and Other N-Heteroarenes with Trichlorosilane
Yun Fu (2019)
10.1002/ANGE.201100008
Ligandengesteuerte hoch regioselektive und asymmetrische Hydrierung von Chinoxalinen, katalysiert durch Ruthenium‐Komplexe von N‐heterocyclischen Carbenen
Slawomir Urban (2011)
10.1002/anie.201207748
Asymmetric hydrogenation of isoquinolinium salts catalyzed by chiral iridium complexes: direct synthesis for optically active 1,2,3,4-tetrahydroisoquinolines.
Atsuhiro Iimuro (2013)
10.1002/ADSC.201600348
A Mixed Ligand Approach for the Asymmetric Hydrogenation of 2-Substituted Pyridinium Salts
M. Renom‐Carrasco (2016)
10.1016/B978-0-12-385235-9.00005-9
Formation of Completely or Partially Reduced Pyridines and Quinolines
Marudai Balasubramanian (2013)
10.1021/ja406761j
Metal-free borane-catalyzed highly stereoselective hydrogenation of pyridines.
Yongbing Liu (2013)
10.1002/anie.201205187
Iridium-catalyzed asymmetric hydrogenation of pyridinium salts.
Zhishi Ye (2012)
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