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

[1] Chelating bis-carbene rhodium(III) complexes in transfer hydrogenation of ketones and imines [J].

Albrecht, M ;

Crabtree, RH ;

Mata, J ;

Peris, E .

CHEMICAL COMMUNICATIONS, 2002, (01) :32-33

[2] Chelated iridium(III) bis-carbene complexes as air-stable catalysts for transfer hydrogenation [J].

Albrecht, M ;

Miecznikowski, JR ;

Samuel, A ;

Faller, JW ;

Crabtree, RH .

ORGANOMETALLICS, 2002, 21 (17) :3596-3604

[3]

Amar H. B., 2010, EUR J INORG CHEM, P4752

[4] Alternative Energy Input for Transfer Hydrogenation using Iridium NHC Based Catalysts in Glycerol as Hydrogen Donor and Solvent [J].

Azua, Arturo ;

Mata, Jose A. ;

Peris, Eduardo ;

Lamaty, Frederic ;

Martinez, Jean ;

Colacino, Evelina .

ORGANOMETALLICS, 2012, 31 (10) :3911-3919

[5] TRITYL TETRAKIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)BORATE - A NEW HYDRIDE ABSTRACTION REAGENT [J].

BAHR, SR ;

BOUDJOUK, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5545-5547

[6] Influence of the anion of the salt used on the coordination mode of an N-heterocyclic carbene ligand to osmium [J].

Baya, Miguel ;

Eguillor, Beatriz ;

Esteruelas, Miguel A. ;

Olivan, Montserrat ;

Onate, Enrique .

ORGANOMETALLICS, 2007, 26 (26) :6556-6563

[7]

Bellemin-Laponnaz S., 2007, COORDIN CHEM REV, P718

[8] R-Allyl Nickel(II) Complexes with Chelating N-Heterocyclic Carbenes: Synthesis, Structural Characterization, and Catalytic Activity [J].

Benitez Junquera, Lourdes ;

Carmen Puerta, M. ;

Valerga, Pedro .

ORGANOMETALLICS, 2012, 31 (06) :2175-2183

[9] ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].

BENNETT, MA ;

SMITH, AK .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02) :233-241

[10] Sulfur-functionalized N-heterocyclic carbenes and their transition metal complexes [J].

Bierenstiel, Matthias ;

Cross, Edward D. .

COORDINATION CHEMISTRY REVIEWS, 2011, 255 (5-6) :574-590

← 1 2 3 4 5 6 7 8 9 10 →