Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst

被引：128
|
作者：
Bruneau-Voisine, Antoine [1 ]
Wang, Ding [1 ]
Dorcet, Vincent [2 ]
Roisnel, Thierry [2 ]
Darcel, Christophe [1 ]
Sortais, Jean-Baptiste [1 ,2 ,3 ,4 ]
机构：
[1] Univ Rennes 1, CNRS, UMR 6226, Inst Sci Chim Rennes,Team Organometall Mat & Cata, 263 Ave Gen Leclerc, F-35042 Rennes, France
[2] Univ Rennes 1, CNRS, UMR 6226, Inst Sci Chim Rennes,Ctr Diffractometrie 10, 263 Ave Gen Leclerc, F-35042 Rennes, France
[3] Inst Univ France, 1 Rue Descartes, F-75231 Paris 5, France
[4] Univ Toulouse, CNRS, LCC, INPT,UPS, 205 Route Narbonne, F-31077 Toulouse 4, France
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 13期
关键词：
WELL-DEFINED MANGANESE; BULKY BIPYRIDINE LIGANDS; PNP PINCER COMPLEXES; CO2; REDUCTION; KETONE HYDROSILYLATION; 2-(AMINOMETHYL) PYRIDINE; ORGANIC-SYNTHESIS; COBALT CATALYSIS; OSMIUM COMPLEXES; PRIMARY ALCOHOLS;
D O I：
10.1021/acs.orglett.7b01657
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A very simple and inexpensive catalytic system based on abundant manganese as transition metal and on an inexpensive phosphine-free bidendate ligand, 2-(aminomethyl)pyridine, has been developed for the reduction of a large variety of carbonyl derivatives with 2-propanol as hydrogen donor. Remarkably, the reaction proceeds at room temperature with low catalyst loading (down to 0.1 mol %) and exhibits a good tolerance toward functional groups. High TON (2000) and TOF (3600 h(-1)) were obtained.
引用
收藏
页码：3656 / 3659
页数：4
相关论文
共 41 条
  • [11] Highly Active Phosphine-Free Bifunctional Iron Complex for Hydrogenation of Bicarbonate and Reductive Amination
    Thai, Trieu-Tien
    Merel, Delphine S.
    Poater, Albert
    Gaillard, Sylvain
    Renaud, Jean-Luc
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (19) : 7066 - 7070
  • [12] Influence of Charge Delocalization on Manganese Catalyzed Transfer Hydrogenation
    Wiedemaier, Fabian
    Hofer, Christa
    Belaj, Ferdinand
    Moesch-Zanetti, Nadia C.
    CHEMCATCHEM, 2024, 16 (07)
  • [13] Highly efficient phosphine-free half-sandwich Ruthenium(II) catalysts for hydrogenation of nitroarenes
    Naveenkumar, K.
    Ravindra, Patil Akshay
    Archana, B.
    Kannan, Neppoliyan
    Pavithran, G.
    Sinha, Arup
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1294
  • [14] Asymmetric transfer hydrogenation of carbonyl compounds catalyzed by rhodium nanoparticles
    Nindakova, Lidiya O.
    Badyrova, Nataliya M.
    Smirnov, Vladimir V.
    Kolesnikov, Sergey S.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 420 : 149 - 158
  • [15] Practical (asymmetric) transfer hydrogenation of ketones catalyzed by manganese with (chiral) diamines ligands
    Wang, Ding
    Bruneau-Voisine, Antoine
    Sortais, Jean-Baptiste
    CATALYSIS COMMUNICATIONS, 2018, 105 : 31 - 36
  • [16] A phosphine-free iron complex-catalyzed synthesis of cycloalkanes via the borrowing hydrogen strategy
    Bettoni, Leo
    Gaillard, Sylvain
    Renaud, Jean-Luc
    CHEMICAL COMMUNICATIONS, 2020, 56 (85) : 12909 - 12912
  • [17] Hydrogenation of Carbon Dioxide to Formic Acid Using PhosPhine-free Non-precious Metal Catalyst
    Takeuchi, Katsuhiko
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (07) : 726 - 727
  • [18] "On Water", Phosphine-Free Palladium-Catalyzed Room Temperature C-H Arylation of Indoles
    Islam, Saidul
    Larrosa, Igor
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (45) : 15093 - 15096
  • [19] Recent Developments in Dehydrogenative Organic Transformations Catalyzed by Homogeneous Phosphine-Free Earth-Abundant Metal Complexes
    Takallou, Ahmad
    Mesgarsaravi, Niloofar
    Beigbaghlou, Somayyeh Sarvi
    Sakhaee, Nader
    Halimehjani, Azim Ziyaei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (03) : 506 - 536
  • [20] Efficient transfer hydrogenation of carbonyl compounds catalyzed by selenophenolato hydrido iron(II) complexes
    Wang, Yangyang
    Du, Zhengyin
    Zheng, Tingting
    Sun, Hongjian
    Li, Xiaoyan
    CATALYSIS COMMUNICATIONS, 2019, 124 : 32 - 35
12345