Ruthenium-Catalyzed Transfer Hydrogenation of Amino- and Amido-Substituted Acetophenones

被引：16

作者：

Watson, Andrew J. A. ^{[1
]}

Fairbanks, Antony J. ^{[1
]}

机构：

[1] Univ Canterbury, Dept Chem, Christchurch 8041, New Zealand

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 30期

关键词：

Ruthenium; Homogeneous catalysis; Hydrogen transfer; Reduction; ASYMMETRIC TRANSFER-HYDROGENATION; ENANTIOSELECTIVE REDUCTION; BORROWING HYDROGEN; KETONES; EFFICIENT; LIGANDS; COMPLEXES; ALCOHOLS; ALDEHYDES; DIAMINE;

D O I：

10.1002/ejoc.201301020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ruthenium-catalyzed transfer hydrogenation of electron-rich amino-substituted acetophenones is reported. Variation of the reductant, ligands, base, and solvent allowed reaction optimization. A key discovery was the use of 1,4-butanediol as an irreversible reducing agent, which significantly improved the conversion. A range of amino- and amido-substituted aryl ketones were explored, and they all gave the corresponding alcohols in good yield, which demonstrates the wider applicability of this process.

引用

页码：6784 / 6788

页数：5

共 50 条

[41] Continuous chirality measure in reaction pathways of ruthenium-catalyzed transfer hydrogenation of ketones [J].

Handgraaf, JW ;

Reek, JNH ;

Bellarosa, L ;

Zerbetto, F .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (06) :792-802

[42] Kinetic Resolution Driven Diastereo- and Enantioselective Synthesis of cis-β-Heteroaryl Amino Cycloalkanols by Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation [J].

Vyas, Vijyesh K. ;

Bhanage, Bhalchandra M. .

ORGANIC LETTERS, 2016, 18 (24) :6436-6439

[43] Designing Vasicine-Derived Ligands and Their Application for Ruthenium-Catalyzed Transfer Hydrogenation Reactions in Water: Synthesis of Amines and Alcohols [J].

Sharma, Sushila ;

Kumar, Manoranjan ;

Nayal, Onkar S. ;

Thakur, Maheshwar S. ;

Bhatt, Vinod ;

Kumar, Neeraj ;

Singh, Bikram ;

Sharma, Upendra .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (12) :1471-1479

[44] Fine-tuning NHC ligands for ruthenium-catalyzed hydrogenation of carboxylic esters to alcohols [J].

Kadyrov, Renat .

JOURNAL OF CATALYSIS, 2023, 426 :173-177

[45] Ruthenium-Catalyzed Conjugate Hydrogenation of α,β-Enones by in situ Generated Dihydrogen from Paraformaldehyde and Water [J].

Li, Wanfang ;

Wu, Xiao-Feng .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (02) :331-335

[46] Stereodivergent Access to Enantioenriched Epoxy Alcohols with Three Stereogenic Centers via Ruthenium-Catalyzed Transfer Hydrogenation [J].

Zhao, Zhifei ;

Bagdi, Prasanta Ray ;

Yang, Shuang ;

Liu, Jinggong ;

Xu, Weici ;

Fang, Xinqiang .

ORGANIC LETTERS, 2019, 21 (14) :5491-5494

[47] Improved Ruthenium-Catalyzed Amination of Alcohols with Ammonia: Synthesis of Diamines and Amino Esters [J].

Imm, Sebastian ;

Baehn, Sebastian ;

Zhang, Min ;

Neubert, Lorenz ;

Neumann, Helfried ;

Klasovsky, Florian ;

Pfeffer, Jan ;

Haas, Thomas ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7599-7603

[48] Ruthenium-Catalyzed Selective Hydrogenation for Flavor and Fragrance Applications [J].

Dupau, Philippe .

ORGANOMETALLICS AS CATALYSTS IN THE FINE CHEMICAL INDUSTRY, 2012, 42 :47-63

[49] Ruthenium-Catalyzed One-Pot Tandem Isomerization-Transfer Hydrogenation Reactions of γ-Trifluoromethylated Allylic Alcohols and β-Trifluoromethylated Enones [J].

Bizet, Vincent ;

Pannecoucke, Xavier ;

Renaud, Jean-Luc ;

Cahard, Dominique .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) :1394-1402

[50] Ruthenium-catalyzed asymmetric reduction of 1,3-diketones using transfer hydrogenation [J].

Cossy, J ;

Eustache, F ;

Dalko, PI .

TETRAHEDRON LETTERS, 2001, 42 (30) :5005-5007

← 1 2 3 4 5 →