Iron(II)-bis(isonitrile) complexes: novel catalysts in asymmetric transfer hydrogenations of aromatic and heteroaromatic ketones

被引:76
作者
Naik, Anu [1 ]
Maji, Tapan [1 ]
Reiser, Oliver [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany
关键词
IRON COMPLEX; POLAR BONDS; LIGANDS;
D O I
10.1039/c0cc00508h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral iron(II)-bis(isonitrile) complexes catalyse the transfer hydrogenation of aromatic ketones with enantioselectivities up to 91% ee, most likely via hydride transfer through imine intermediates, generated by in situ reduction of the isonitrile ligands, whereas iron acts as a Lewis acid to activate the ketone.
引用
收藏
页码:4475 / 4477
页数:3
相关论文
共 22 条
[1]   AN EXCEPTIONALLY STABLE CIS-(HYDRIDE)(ETA-2-DIHYDROGEN) COMPLEX OF IRON [J].
BIANCHINI, C ;
PERUZZINI, M ;
ZANOBINI, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 354 (02) :C19-C22
[2]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[3]   [Fe(CNXyl)4]2-:: An isolable and structurally characterized homoleptic isocyanidemetalate dianion [J].
Brennessel, William W. ;
Ellis, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (04) :598-600
[4]   Efficient transfer hydrogenation of ketones catalyzed by the bis(isocyanide)-ruthenium(II) complexes trans, cis,cis-[RuX2(CNR)2(dppf)] (X = Cl, Br; dppf = 1,1′-bis(diphenylphosphino)ferrocene):: Isolation of active mono- and dihydride intermediates [J].
Cadierno, V ;
Crochet, P ;
Díez, J ;
García-Garrido, SE ;
Gimeno, J .
ORGANOMETALLICS, 2004, 23 (21) :4836-4845
[5]   Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].
Clapham, SE ;
Hadzovic, A ;
Morris, RH .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237
[6]   Sustainable metal catalysis with iron: From rust to a rising star? [J].
Enthaler, Stephan ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3317-3321
[7]   Biomimetic transfer hydrogenation of ketones with iron porphyrin catalysts [J].
Enthaler, Stephan ;
Erre, Giulia ;
Tse, Man Kin ;
Junge, Kathrin ;
Beller, Matthias .
TETRAHEDRON LETTERS, 2006, 47 (46) :8095-8099
[8]   Iron-Catalyzed Hydrogenation, Hydride Transfer, and Hydrosilylation: An Alternative to Precious-Metal Complexes? [J].
Gaillard, Sylvain ;
Renaud, Jean-Luc .
CHEMSUSCHEM, 2008, 1 (06) :505-509
[9]   Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular [J].
Ikariya, Takao ;
Blacker, A. John .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1300-1308
[10]   Iridium catalysts with bicyclic pyridine-phosphinite ligands: Asymmetric hydrogenation of olefins and furan derivatives [J].
Kaiser, Stefan ;
Smidt, Sebastian R. ;
Pfaltz, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (31) :5194-5197