Acetate Acetylacetonate Ampy Ruthenium(II) Complexes as Efficient Catalysts for Ketone Transfer Hydrogenation

被引:13
作者
Hey, Daniela A. [1 ,2 ]
Sauer, Michael J. [1 ,2 ]
Fischer, Pauline J. [1 ,2 ]
Esslinger, Eva-Maria H. J. [1 ,2 ]
Kuehn, Fritz E. [1 ,2 ]
Baratta, Walter [3 ]
机构
[1] Tech Univ Munich, Mol Catalysis, Catalysis Res Ctr, Lichtenbergstr 4, D-85748 Munich, Germany
[2] Tech Univ Munich, Dept Catalysis, Lichtenbergstr 4, D-85748 Munich, Germany
[3] Univ Udine, Dipartimento Sci AgroAlimentari Ambientali & Anim, Via Cotonificio 108, I-33100 Udine, Italy
关键词
acetylacetonate; 2-(aminomethyl)pyridine; hydrogenation; ruthenium complexes; transfer hydrogenation; ASYMMETRIC HYDROGENATION; PINCER; ALCOHOLS; MECHANISM; BEHAVIOR; LIGANDS;
D O I
10.1002/cctc.202000542
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The mixed acetate acetylacetonate (acac) ruthenium(II) phosphine complexes Ru(OAc)(acac)P-2 [P-2=(PPh3)(2), Ph2P(CH2)(4)PPh2 (dppb)] were prepared by protonation of Ru(OAc)(2)(PPh3)(2) with acetylacetone in dichloromethane. Reaction of the dppb derivative with 2-(aminomethyl)pyridine (ampy) affords the complex Ru(OAc)(acac)(ampy)(dppb), which converts to [Ru(acac)(ampy)(dppb)](OAc) in toluene at 90 degrees C. In the former derivative the ampy ligand is monodentate and coordinates through the NH2-moiety. The isolated acac complexes are active catalysts for the transfer hydrogenation of ketones with loadings as low as 0.01 mol%, the ampy having a strong accelerating effect. Several aromatic and aliphatic ketone substrates are converted to their corresponding alcohols, and different electronic influences through substituents on acetophenone are tolerated.
引用
收藏
页码:3537 / 3544
页数:8
相关论文
共 36 条
[1]   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
[2]   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
[3]   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
[4]   CNN Pincer Ruthenium Catalysts for Hydrogenation and Transfer Hydrogenation of Ketones: Experimental and Computational Studies [J].
Baratta, Walter ;
Baldino, Salvatore ;
Calhorda, Maria Jose ;
Costa, Paulo J. ;
Esposito, Gennaro ;
Herdtweck, Eberhardt ;
Magnolia, Santo ;
Mealli, Carlo ;
Messaoudi, Abdelatif ;
Mason, Sax A. ;
Veiros, Luis F. .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (42) :13603-13617
[5]   Pincer CNN Ruthenium(II) Complexes with Oxygen-Containing Ligands (O2CR, OAr, OR, OSiR3, O3SCF3): Synthesis, Structure, and Catalytic Activity in Fast Transfer Hydrogenation [J].
Baratta, Walter ;
Ballico, Maurizio ;
Del Zotto, Alessandro ;
Herdtweck, Eberhardt ;
Magnolia, Santo ;
Peloso, Riccardo ;
Siega, Katia ;
Toniutti, Micaela ;
Zangrando, Ennio ;
Rigo, Pierluigi .
ORGANOMETALLICS, 2009, 28 (15) :4421-4430
[6]   Bis(acetylacetonato)ruthenium(II) complexes containing bulky tertiary phosphines.: Formation and redox behaviour of Ru(acac)2 (PR3) (R = iPr, Cy) complexes with ethene, carbon monoxide, and bridging dinitrogen [J].
Bennett, MA ;
Byrnes, MJ ;
Chung, G ;
Edwards, AJ ;
Willis, AC .
INORGANICA CHIMICA ACTA, 2005, 358 (05) :1692-1708
[7]   Bis(acetylacetonato)bis(cyclooctene)ruthenium(II), cis-[Ru(acac)2(η2-C8H14)2]:: a synthetic precursor to trans- and cis-bis(acetylacetonato)ruthenium(II) complexes [J].
Bennett, MA ;
Chung, GL ;
Hockless, DCR ;
Neumann, H ;
Willis, AC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (19) :3451-3462
[8]   PHOSPHINE-SUBSTITUTED RUTHENIUM CARBONYL CARBOXYLATES [J].
BIANCHI, M ;
FREDIANI, P ;
MATTEOLI, U ;
MENCHI, G ;
PIACENTI, F ;
PETRUCCI, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 259 (02) :207-214
[9]   Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines [J].
Cabrero-Antonino, Jose R. ;
Alberico, Elisabetta ;
Junge, Kathrin ;
Junge, Henrik ;
Beller, Matthias .
CHEMICAL SCIENCE, 2016, 7 (05) :3432-3442
[10]   Ruthenium and osmium complexes containing 2-(aminomethyl)pyridine (Ampy)-based ligands in catalysis [J].
Chelucci, Giorgio ;
Baldino, Salvatore ;
Baratta, Walter .
COORDINATION CHEMISTRY REVIEWS, 2015, 300 :29-85