Phosphine-free chiral iridium catalysts for asymmetric catalytic hydrogenation of simple ketones

被引:3
|
作者
Kumar, Prashant [1 ,2 ]
Irrgang, Torsten [2 ]
Kostakis, George E. [1 ]
Kempe, Rhett [2 ]
机构
[1] Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QJ, E Sussex, England
[2] Univ Bayreuth, Inorgan Chem 2, POB 101251, D-95440 Bayreuth, Germany
来源
RSC ADVANCES | 2016年 / 6卷 / 45期
关键词
OPPORTUNITIES NOBEL LECTURE; HOMOGENEOUS HYDROGENATION; RUTHENIUM COMPLEXES; ENANTIOSELECTIVE HYDROGENATION; STEREOSELECTIVE HYDROGENATION; DIOLEFIN COMPLEXES; AROMATIC KETONES; LIGANDS; MECHANISM; SCIENCE;
D O I
10.1039/c6ra04524c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel pyridylalkylamine and aminopyridinato ligand stabilized iridium complexes with no P ligand are introduced. These complexes have been investigated as catalysts for asymmetric hydrogenation of simple ketones, resulting in an active catalyst for bulky alkyl aryl ketones that is alpha-methylpropiophenone. The ligands were synthesized from inexpensive starting materials and their modular design allows for the introduction of a broad variety of substitution patterns. Additionally, better activity and selectivity was observed at 20 degrees C and 20 bar H-2 pressure with a catalyst loading as low as 0.05 mol% iridium. These phosphorus free catalysts have always been a central issue in both academic and industrial research.
引用
收藏
页码:39335 / 39342
页数:8
相关论文
共 50 条
  • [1] Phosphine-free chiral metal catalysts for highly effective asymmetric catalytic hydrogenation
    He, Yan-Mei
    Fan, Qing-Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (11) : 2497 - 2504
  • [2] Asymmetric Hydrogenation of N-Alkyl Ketimines with Phosphine-Free, Chiral, Cationic Ru-MsDPEN Catalysts
    Chen, Fei
    Wang, Tianli
    He, Yanmei
    Ding, Ziyuan
    Li, Zhiwei
    Xu, Lijin
    Fan, Qing-Hua
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (04) : 1109 - 1113
  • [3] Asymmetric Hydrogenation of Cyclic N-Sulfonylimines with Phosphine-Free Chiral Cationic Ru-MsDPEN Catalysts
    Chen Fei
    Li Zhiwei
    He Yanmei
    Fan Qinghua
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (09) : 1529 - 1532
  • [4] The Development of Phosphine-Free Tethered Ruthenium(II) Catalysts for the Asymmetric Reduction of Ketones and Imines
    Nedden, Hans G.
    Zanotti-Gerosa, Antonio
    Wills, Martin
    CHEMICAL RECORD, 2016, 16 (06): : 2623 - 2643
  • [5] Iridium Catalysts with f-Amphox Ligands: Asymmetric Hydrogenation of Simple Ketones
    Wu, Weilong
    Liu, Shaodong
    Duan, Meng
    Tan, Xuefeng
    Chen, Caiyou
    Xie, Yun
    Lan, Yu
    Dong, Xin-Qin
    Zhang, Xumu
    ORGANIC LETTERS, 2016, 18 (12) : 2938 - 2941
  • [6] Air-Stable and Phosphine-Free Iridium Catalysts for Highly Enantioselective Hydrogenation of Quinoline Derivatives
    Li, Zhi-Wei
    Wang, Tian-Li
    He, Yan-Mei
    Wang, Zhi-Jian
    Fan, Qing-Hua
    Pan, Jie
    Xu, Li-Jun
    ORGANIC LETTERS, 2008, 10 (22) : 5265 - 5268
  • [7] Asymmetric Hydrogenation of Ketones——Design of Chiral Catalysts
    Takeshi Ohkuma
    复旦学报(自然科学版), 2005, (05) : 152 - 153
  • [8] Phosphine-free Cp*Ru(diamine) catalysts in the hydrogenation of imines
    Cheruku, Pradeep
    Church, Tamara L.
    Andersson, Pher G.
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1390 - 1394
  • [9] Efficient asymmetric transfer hydrogenation of ketones in ethanol with chiral iridium complexes of spiroPAP ligands as catalysts
    Liu, Wei-Peng
    Yuan, Ming-Lei
    Yang, Xiao-Hui
    Li, Ke
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CHEMICAL COMMUNICATIONS, 2015, 51 (28) : 6123 - 6125
  • [10] An Additional Coordination Group Leads to Extremely Efficient Chiral Iridium Catalysts for Asymmetric Hydrogenation of Ketones
    Xie, Jian-Hua
    Liu, Xiao-Yan
    Xie, Jian-Bo
    Wang, Li-Xin
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) : 7329 - 7332