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

被引:127
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
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 67 条
[1]   Intramolecular carboboration of carbonyl ligands to form boroxycarbenes [J].
Alvarez, Celedonio M. ;
Carrillo, Romen ;
Garcia-Rodriguez, Raul ;
Miguel, Daniel .
CHEMICAL COMMUNICATIONS, 2012, 48 (62) :7705-7707
[2]   A Stable Manganese Pincer Catalyst for the Selective Dehydrogenation of Methanol [J].
Anderez-Fernandez, Maria ;
Vogt, Lydia K. ;
Fischer, Steffen ;
Zhou, Wei ;
Jiao, Haijun ;
Garbe, Marcel ;
Elangovan, Saravanakumar ;
Junge, Kathrin ;
Junge, Henrik ;
Ludwig, Ralf ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (02) :559-562
[3]  
[Anonymous], CATALYSIS PRECIOUS M
[4]   Metal-Catalyzed Reduction of HCONR2′, R′ = Me (DMF), Et (DEF), by Silanes to Produce R2′NMe and Disiloxanes: A Mechanism Unraveled [J].
Arias-Ugarte, Renzo ;
Sharma, Hemant K. ;
Morris, Andrew L. C. ;
Pannell, Keith H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :848-851
[5]   Transfer Hydrogenation and Hydrogenation of Commercial-Grade Aldehydes to Primary Alcohols Catalyzed by 2-(Aminomethyl) pyridine and Pincer Benzo[h]quinoline Ruthenium Complexes [J].
Baldino, Salvatore ;
Facchetti, Sarah ;
Zanotti-Gerosa, Antonio ;
Nedden, Hans Gunter ;
Baratta, Walter .
CHEMCATCHEM, 2016, 8 (13) :2279-2288
[6]   2-(Aminomethyl)pyridine-phosphine ruthenium(II) complexes: Novel highly active transfer hydrogenation catalysts [J].
Baratta, W ;
Herdtweck, E ;
Siega, K ;
Toniutti, M ;
Rigo, P .
ORGANOMETALLICS, 2005, 24 (07) :1660-1669
[7]   1-(pyridin-2-yl)methanamine-based ruthenium catalysts for fast transfer hydrogenation of carbonyl compounds in 2-propanol [J].
Baratta, Walter ;
Rigo, Pierluigi .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2008, (26) :4041-4053
[8]  
Bauer E, 2015, TOP ORGANOMETAL CHEM, V50, pV
[9]   Iron Catalysis in Organic Synthesis [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387
[10]   [Mn(bipyridyl)(CO)3Br]: An Abundant Metal Carbonyl Complex as Efficient Electrocatalyst for CO2 Reduction [J].
Bourrez, Marc ;
Molton, Florian ;
Chardon-Noblat, Sylvie ;
Deronzier, Alain .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (42) :9903-9906