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

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

[41] Direct Access to POP-Type Osmium(II) and Osmium(IV) Complexes: Osmium a Promising Alternative to Ruthenium for the Synthesis of Imines from Alcohols and Amines [J].

Esteruelas, Miguel A. ;

Honczek, Nicole ;

Olivan, Montserrat ;

Onate, Enrique ;

Valencia, Marta .

ORGANOMETALLICS, 2011, 30 (09) :2468-2471

[42]

Farrugia L.J., 1997, J. Appl. Crystallogr., V30, P565, DOI [10.1107/S0021889897003117, DOI 10.1107/S0021889897003117]

[43] Half-Sandwich Ruthenium(II) Picolyl-NHC Complexes: Synthesis, Characterization, and Catalytic Activity in Transfer Hydrogenation Reactions [J].

Fernandez, Francys E. ;

Carmen Puerta, M. ;

Valerga, Pedro .

ORGANOMETALLICS, 2011, 30 (21) :5793-5802

[44] Thioether-Functionalized N-Heterocyclic Carbenes: Mono- and Bis-(S,CNHC) Palladium Complexes, Catalytic C-C Coupling, and Characterization of a Unique Ag4I4 (S,CNHC)2 Planar Cluster [J].

Fliedel, Christophe ;

Braunstein, Pierre .

ORGANOMETALLICS, 2010, 29 (21) :5614-5626

[45] Synthesis of N,N′-bis(thioether)-functionalized imidazolium salts: their reactivity towards Ag and Pd complexes and first S,CNHC,S free carbene [J].

Fliedel, Christophe ;

Sabbatini, Alessandra ;

Braunstein, Pierre .

DALTON TRANSACTIONS, 2010, 39 (37) :8820-8828

[46] Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines [J].

Fujita, Ken-ichi ;

Enoki, Youichiro ;

Yamaguchi, Ryohei .

TETRAHEDRON, 2008, 64 (08) :1943-1954

[47] Chelating NHC Ruthenium(II) Complexes as Robust Homogeneous Hydrogenation Catalysts [J].

Gandolfi, Claudio ;

Heckenroth, Marion ;

Neels, Antonia ;

Laurenczy, Gabor ;

Albrecht, Martin .

ORGANOMETALLICS, 2009, 28 (17) :5112-5121

[48] CONVERSION OF LONG-CHAIN TERMINAL ALCOHOLS AND SECONDARY-AMINES INTO TERTIARY-AMINES USING RUTHENIUM(II) TERTIARY PHOSPHINE COMPLEXES AS HOMOGENEOUS CATALYSTS [J].

GANGULY, S ;

ROUNDHILL, DM .

POLYHEDRON, 1990, 9 (20) :2517-2526

[49] [Ru(bpy)3]2+ Analogues Containing an N-Heterocyclic Carbene Ligand [J].

Ghattas, Wadih ;

Bunz, Helge Muller ;

Albrecht, Martin .

ORGANOMETALLICS, 2010, 29 (24) :6782-6789

[50] Direct Amide Synthesis from Alcohols and Amines by Phosphine-Free Ruthenium Catalyst Systems [J].

Ghosh, Subhash Chandra ;

Muthaiah, Senthilkumar ;

Zhang, Yao ;

Xu, Xiangya ;

Hong, Soon Hyeok .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) :2643-2649

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