Propylene carbonate as a solvent for asymmetric Hydrogenations

被引：243

作者：

Bayardon, Jerome ^{[1
]}

Holz, Jens ^{[1
]}

Schaeffner, Benjamin ^{[1
]}

Andrushko, Vasyl ^{[1
]}

Verevkin, Sergej ^{[1
]}

Preetz, Angelika ^{[1
]}

Boerner, Armin ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 31期

关键词：

asymmetric catalysis; green chemistry; hydrogenations; iridium; solvent effects;

D O I：

10.1002/anie.200700990

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) A penny saved is a penny earned: The use of propylene carbonate as the solvent in iridium-catalyzed hydrogenations of non-functionalized olefins allows efficient catalyst recycling through the formation of two-phase mixtures with nonpolar solvents such as n-hexane. In the picture, the hydrogenated tetrahydronaphthalene derivative is extracted into the hydrocarbon phase. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5971 / 5974

页数：4

共 34 条

[21] CATIONIC BINAP-RU(II) HALIDE-COMPLEXES - HIGHLY EFFICIENT CATALYSTS FOR STEREOSELECTIVE ASYMMETRIC HYDROGENATION OF ALPHA-FUNCTIONALIZED AND BETA-FUNCTIONALIZED KETONES [J].

MASHIMA, K ;

KUSANO, KH ;

SATO, N ;

MATSUMURA, Y ;

NOZAKI, K ;

KUMOBAYASHI, H ;

SAYO, N ;

HORI, Y ;

ISHIZAKI, T ;

AKUTAGAWA, S ;

TAKAYA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3064-3076

[22] Iridium-catalyzed enantioselective hydrogenation of terminal alkenes [J].

McIntyre, S ;

Hörmann, E ;

Menges, F ;

Smidt, SP ;

Pfaltz, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :282-288

[23]

Menges F, 2002, ADV SYNTH CATAL, V344, P40, DOI 10.1002/1615-4169(200201)344:1<40::AID-ADSC40>3.0.CO

[24]

2-7

[25] SYNTHESIS OF 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP), AN ATROPISOMERIC CHIRAL BIS(TRIARYL)PHOSPHINE, AND ITS USE IN THE RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF ALPHA-(ACYLAMINO)ACRYLIC ACIDS [J].

MIYASHITA, A ;

YASUDA, A ;

TAKAYA, H ;

TORIUMI, K ;

ITO, T ;

SOUCHI, T ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7932-7934

[26] Synthesis and application of chiral N-heterocyclic carbene-oxazoline ligands:: Iridium-catalyzed enantioselective hydrogenation [J].

Nanchen, Steve ;

Pfaltz, Andreas .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (17) :4550-4558

[27] Propylene carbonate stabilized nanostructured palladium clusters as catalysts in Heck reactions [J].

Reetz, MT ;

Lohmer, G .

CHEMICAL COMMUNICATIONS, 1996, (16) :1921-1922

[28] SimplePHOX, a readily available chiral ligand system for iridium-catalyzed asymmetric hydrogenation [J].

Smidt, SP ;

Menges, F ;

Pfaltz, A .

ORGANIC LETTERS, 2004, 6 (12) :2023-2026

[29] Kinetic influences on enantioselectivity in asymmetric catalytic hydrogenation [J].

Sun, YK ;

Wang, J ;

LeBlond, C ;

Landau, RN ;

Laquidara, J ;

Sowa, JR ;

Blackmond, DG .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 115 (03) :495-502

[30] Observation of a [RuCl2((S)-((-))-tol-binap)](2)center dot N(C2H5)(3)-catalyzed isomerization-hydrogenation network [J].

Sun, YK ;

LeBlond, C ;

Wang, J ;

Blackmond, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (50) :12647-12648

← 1 2 3 4 →