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

被引：128

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

来源：

ORGANOMETALLICS | 2012年 / 31卷 / 19期

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

页码：6868 / 6879

页数：12

共 149 条

[61] Synthesis, Characterization, and H-Bonding Abilities of Ruthenium(II) Complexes Bearing Bidentate NR,NH-Carbene/Phosphine Ligands
Hahn, F. Ekkehardt
Naziruddin, Abbas Raja
Hepp, Alexander
Pape, Tania
[J]. ORGANOMETALLICS, 2010, 29 (21) : 5283 - 5288
[62] Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology
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.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) : 1766 - 1774
[63] Ruthenium catalysed N-alkylation of amines with alcohols
Hamid, Malai Haniti S. A.
Williams, Jonathan M. J.
[J]. CHEMICAL COMMUNICATIONS, 2007, (07) : 725 - 727
[64] Industrial processes for manufacturing amines
Hayes, KS
[J]. APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) : 187 - 195
[65] Functionalized imidazoline-2-ylidene complexes of rhodium and palladium
Herrmann, WA
Goossen, LJ
Spiegler, M
[J]. 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
Herrmann, WA
Elison, M
Fischer, J
Kocher, C
Artus, GRJ
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (07) : 772 - 780
[69] An improved ruthenium catalyst for the environmentally benign amination of primary and secondary alcohols
Hollmann, Dirk
Tillack, Annegret
Michalik, Dirk
Jackstell, Ralf
Beller, Matthias
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (03) : 403 - 410
[70] Transfer Hydrogenation of Ketones and Activated Olefins Using Chelating NHC Ruthenium Complexes
Horn, Sabine
Gandolfi, Claudio
Albrecht, Martin
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (18) : 2863 - 2868

← 2 3 4 5 6 7 8 9 10 11 →