Quinoline-functionalized N-heterocyclic carbene complexes of iridium: Synthesis, structures and catalytic activities in transfer hydrogenation

被引:37
作者
Sun, Jia-Feng [1 ]
Chen, Fei [1 ]
Dougan, Brenda A. [2 ]
Xu, Hui-Jun [1 ]
Cheng, Yong [1 ]
Li, Yi-Zhi [1 ]
Chen, Xue-Tai [1 ]
Xue, Zi-Ling [2 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing Natl Lab Microstruct, Coordinat Chem Inst,State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China
[2] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA
基金
美国国家科学基金会;
关键词
N-heterocyclic carbene; Iridium; Transfer hydrogenation; Catalysis; ASYMMETRIC TRANSFER HYDROGENATION; COORDINATION CHEMISTRY; COPPER(II) COMPLEXES; CRYSTAL-STRUCTURES; LINKED CYCLOPHANE; SILVER COMPLEX; LIGANDS; RHODIUM; DYNAMICS; HYDROSILYLATION;
D O I
10.1016/j.jorganchem.2009.02.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Iridium complexes containing quinoline-functionalized N-heterocyclic carbene (NHC) ligands have been synthesized by the transmetalation route from silver carbene precursors. The silver complexes undergo a facile reaction with [Ir(COD)Cl](2) (COD = 1,5-cyclooctadiene) to yield a series of carbene complexes [(NHC)Ir(COD)Cl] (NHC = 3-methyl-1-(8- quinolylmethyl)imidazole-2-ylidene (2a); 3-n-butyl-1-(8-quinolylmethyl)imidazole-2-ylidene (2b); 3-benzyl-1-(8-quinolylmethyl)imidazole-2-ylidene (2c); 1,3-di(8-quinolylmethyl)imidazole-2- ylidene (2d). The coordinated COD was replaced by carbon monoxide to yield the corresponding carbonyl species [(NHC)Ir(CO)(2)Cl] (3). Complexes 2 and 3 have been characterized by IR, ESI-MS, H-1 and C-13 NMR and elemental analyses. The molecular structures of complexes 2b and 2c have been confirmed by single-crystal X-ray diffraction. Two analogous Ir(I) complexes 5 and 6 with naphthalene-containing NHC have also been synthesized and characterized. These Ir(I) complexes in the current work have been proved to be active catalysts in the transfer hydrogenation of ketones to alcohols using 2-propanol as the hydrogen source. (c) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:2096 / 2105
页数:10
相关论文
共 65 条
[1]   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
[2]   N-heterocyclic carbenes. 49. Chiral N-heterocyclic carbenes with restricted flexibility in asymmetric catalysis [J].
Baskakov, Denys ;
Herrmann, Wolfgang A. ;
Herdtweck, Eberhardt ;
Hoffmann, Stephan D. .
ORGANOMETALLICS, 2007, 26 (03) :626-632
[3]   Selective hydrogenation for fine chemicals: Recent trends and new developments [J].
Blaser, HU ;
Malan, C ;
Pugin, B ;
Spindler, F ;
Steiner, H ;
Studer, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151
[4]  
Boeda F, 2008, ANNU REP PROG CHEM B, V104, P184, DOI 10.1039/b716604b
[5]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[6]   NEW 1,4,7,10-TETRAAZACYCLOTRIDECANE-11,13-DIONE LIGANDS APPENDED WITH ADDITIONAL DONOR(S) 8-METHYLQUINOLINE(S) - CRYSTAL-STRUCTURES AND CHARACTERIZATION OF THEIR COPPER(II) COMPLEXES [J].
BU, XH ;
AN, DL ;
CHEN, YT ;
SHIONOYA, M ;
KIMURA, E .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1995, (13) :2289-2295
[7]   Rhodium and iridium complexes of N-heterocyclic carbenes via transmetalation: Structure and dynamics [J].
Chianese, AR ;
Li, XW ;
Janzen, MC ;
Faller, JW ;
Crabtree, RH .
ORGANOMETALLICS, 2003, 22 (08) :1663-1667
[8]   Axially chiral bidentate N-heterocyclic carbene ligands derived from BINAM: rhodium and iridium complexes in asymmetric ketone hydrosilylation [J].
Chianese, AR ;
Crabtree, RH .
ORGANOMETALLICS, 2005, 24 (18) :4432-4436
[9]   Abnormal C5-bound N-heterocyclic carbenes: Extremely strong electron donor ligands and their iridium(I) and iridium(III) complexes [J].
Chianese, AR ;
Kovacevic, A ;
Zeglis, BM ;
Faller, JW ;
Crabtree, RH .
ORGANOMETALLICS, 2004, 23 (10) :2461-2468
[10]   Structural variations in novel silver(I) complexes with bitopic pyrazole/N-heterocyclic carbene ligands [J].
Chiu, PL ;
Chen, CY ;
Lee, CC ;
Hsieh, MH ;
Chuang, CH ;
Lee, HM .
INORGANIC CHEMISTRY, 2006, 45 (06) :2520-2530