Phosphine-Imidazolyl Ligands for the Efficient Ruthenium-Catalyzed Hydrogenation of Carboxylic Esters

被引:44
|
作者
Junge, Kathrin [1 ]
Wendt, Bianca [1 ]
Westerhaus, Felix Alexander [1 ]
Spannenberg, Anke [1 ]
Jiao, Haijun [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
alcohols; esters; hydrogenation; ligand design; ruthenium; GAUSSIAN-BASIS SETS; ENANTIOSELECTIVE HYDROGENATION; CHEMOSELECTIVE REDUCTION; ASYMMETRIC-SYNTHESIS; ATOMS LI; COMPLEXES; AMIDES; CONVENIENT; ALCOHOLS; AMINES;
D O I
10.1002/chem.201200408
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of phosphineimidazolyl ligands 1 and 2 in good yields is presented. In combination with [{Ru(benzene)Cl2}2], ligands 1?c and 1?e formed efficient catalyst systems for the selective hydrogenation of various carboxylic esters into their corresponding primary alcohols. Furthermore, the structures of four ruthenium complexes with ligands 1?b, 1?c, 1?d, and 1?e were determined by X-ray crystallography, which showed the formation of different coordination modes depending on the ligand structure.
引用
收藏
页码:9011 / 9018
页数:8
相关论文
共 50 条
  • [1] Ruthenium-Catalyzed Selective Reduction of Carboxylic Esters and Carboxamides
    Zhou, Yongyun
    Khan, Ruhima
    Fan, Baomin
    Xu, Lijin
    SYNTHESIS-STUTTGART, 2019, 51 (12): : 2491 - 2505
  • [2] Fine-tuning NHC ligands for ruthenium-catalyzed hydrogenation of carboxylic esters to alcohols
    Kadyrov, Renat
    JOURNAL OF CATALYSIS, 2023, 426 : 173 - 177
  • [3] Direct Ruthenium-Catalyzed Hydrogenation of Carboxylic Acids to Alcohols
    Cui, Xinjiang
    Li, Yuehui
    Topf, Christoph
    Junge, Kathrin
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (36) : 10596 - 10599
  • [4] A Mild and Base-Free Protocol for the Ruthenium-Catalyzed Hydrogenation of Aliphatic and Aromatic Nitriles with Tridentate Phosphine Ligands
    Adam, Rosa
    Bheeter, Charles Beromeo
    Jackstell, Ralf
    Beller, Matthias
    CHEMCATCHEM, 2016, 8 (07) : 1329 - 1334
  • [5] Suitable ligands for homogeneous ruthenium-catalyzed hydrogenolysis of esters
    van Engelen, MC
    Teunissen, HT
    de Vries, JG
    Elsevier, CJ
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 206 (1-2) : 185 - 192
  • [6] Ruthenium-catalysed hydrogenation of esters using tripodal phosphine ligands
    Hanton, Martin J.
    Tin, Sergey
    Boardman, Brian.
    Miller, Philip
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 346 (1-2) : 70 - 78
  • [7] Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
    Yuan, Ming-Lei
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CHEMCATCHEM, 2016, 8 (19) : 3036 - 3040
  • [8] Highly Efficient Ruthenium-Catalyzed Semi-hydrogenation of Urea Derivatives to Formamides
    Zhu, Jun
    Zhang, Yue
    Wen, Zeyu
    Ma, Qiyi
    Wang, Yongtao
    Yao, Jia
    Li, Haoran
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (31)
  • [9] Hydrogenation of carboxylic esters catalyzed by manganese catalysts supported by bidentate NHC-phosphine ligands
    Azouzi, Karim
    Pointis, Romane
    Buhaibeh, Ruqaya
    Fernandez, Pablo Hermosilla
    Pedussaut, Lucie
    Boundor, Mohamed
    Bonfiglio, Anna
    Bruneau-Voisine, Antoine
    Wei, Duo
    Roisnel, Thierry
    Duhayon, Carine
    Casado, Miguel Angel
    Valyaev, Dmitry A.
    Canac, Yves
    Bastin, Stephanie
    Raynaud, Christophe
    Sortais, Jean -Baptiste
    JOURNAL OF CATALYSIS, 2024, 430
  • [10] Benzimidazoles as Ligands in the Ruthenium-Catalyzed Enantioselective Bifunctional Hydrogenation of Ketones
    Praetorius, Jeremy M.
    Wang, Ruiyao
    Crudden, Cathleen M.
    ORGANOMETALLICS, 2010, 29 (03) : 554 - 561