Ruthenium(II) Picolyl-NHC Complexes: Synthesis, Characterization, and Catalytic Activity in Amine N-alkylation and Transfer Hydrogenation Reactions

被引:129
作者
Fernandez, Francys E. [1 ]
Carmen Puerta, M. [1 ]
Valerga, Pedro [1 ]
机构
[1] Univ Cadiz, Fac Ciencias, Dept Ciencia Mat & Ingn Met & Quim Inorgan, Cadiz 11510, Spain
关键词
HETEROCYCLIC-CARBENE COMPLEXES; C-H ACTIVATION; EFFICIENT CATALYSTS; NICKEL(II) COMPLEXES; POLYMERIZATION BEHAVIOR; RHODIUM(I) COMPLEXES; PALLADIUM COMPLEXES; BORROWING HYDROGEN; IRIDIUM COMPLEXES; RU(II) COMPLEXES;
D O I
10.1021/om300692a
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ruthenium(II) p-cymene complexes with picolyl-functionalized N-heterocyclic carbenes [(eta(6)-p-cymene)Ru(L)(Cl)]-[PF6] (L = 3-methyl-1-(2-picolyl)imidazol-2-ylidene (1a), 3-isopropyl-1-(2-picolyl)imidazol-2-ylidene (1b), 3,4,5-trimethyl-1-(2-picoly)imidazol-2-ylidene (1c), 3-mesityl-1-(2-picolyl)imidazol-2-ylidene (1d), 3-methyl-1-(2-picolyl)benzoimidazol-2-ylidene (1f), 3-methyl-1-(2-picolyl)-4,5-dichloroimidazol-2-ylidene (1f), 3-phenyl-1-(2-picolyl)imidazol-2-ylidene (1g)) have been synthesized and characterized. Compounds 1 a-g were recrystallized, and X-ray crystal structures are reported for 1a,f. Furthermore, compounds 1a-f show catalytic activity in transfer hydrogenation of ketones and N-alkylation of amines. Notably, complexes 1a,c,f were found to be very efficient and versatile catalysts toward transfer hydrogenation of a wide range of ketones and imines in addition to N-alkylation of several amines.
引用
收藏
页码:6868 / 6879
页数:12
相关论文
共 149 条
[61]   Synthesis, Characterization, and H-Bonding Abilities of Ruthenium(II) Complexes Bearing Bidentate NR,NH-Carbene/Phosphine Ligands [J].
Hahn, F. Ekkehardt ;
Naziruddin, Abbas Raja ;
Hepp, Alexander ;
Pape, Tania .
ORGANOMETALLICS, 2010, 29 (21) :5283-5288
[62]   Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology [J].
Hamid, M. Haniti S. A. ;
Allen, C. Liana ;
Lamb, Gareth W. ;
Maxwell, Aoife C. ;
Maytum, Hannah C. ;
Watson, Andrew J. A. ;
Williams, Jonathan M. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) :1766-1774
[63]   Ruthenium catalysed N-alkylation of amines with alcohols [J].
Hamid, Malai Haniti S. A. ;
Williams, Jonathan M. J. .
CHEMICAL COMMUNICATIONS, 2007, (07) :725-727
[64]   Industrial processes for manufacturing amines [J].
Hayes, KS .
APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) :187-195
[65]   Functionalized imidazoline-2-ylidene complexes of rhodium and palladium [J].
Herrmann, WA ;
Goossen, LJ ;
Spiegler, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 547 (02) :357-366
[66]  
Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
[67]  
2-Y
[68]   N-heterocyclic carbenes([+]): Generation under mild conditions and formation of group 8-10 transition metal complexes relevant to catalysis [J].
Herrmann, WA ;
Elison, M ;
Fischer, J ;
Kocher, C ;
Artus, GRJ .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (07) :772-780
[69]   An improved ruthenium catalyst for the environmentally benign amination of primary and secondary alcohols [J].
Hollmann, Dirk ;
Tillack, Annegret ;
Michalik, Dirk ;
Jackstell, Ralf ;
Beller, Matthias .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (03) :403-410
[70]   Transfer Hydrogenation of Ketones and Activated Olefins Using Chelating NHC Ruthenium Complexes [J].
Horn, Sabine ;
Gandolfi, Claudio ;
Albrecht, Martin .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (18) :2863-2868