Iron Achieves Noble Metal Reactivity and Selectivity: Highly Reactive and Enantioselective Iron Complexes as Catalysts in the Hydrosilylation of Ketones

被引:118
作者
Bleith, Tim [1 ]
Wadepohl, Hubert [1 ]
Gade, Lutz H. [1 ]
机构
[1] Heidelberg Univ, Inst Anorgan Chem, D-69120 Heidelberg, Germany
关键词
ASYMMETRIC TRANSFER HYDROGENATION; PINCER LIGANDS; CARBONYL-COMPOUNDS; REDUCTION; PROTOCOL; ESTERS;
D O I
10.1021/ja512986m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral iron alkyl and iron alkoxide complexes bearing boxmi pincers as stereodirecting ligands have been employed as catalysts for enantioselective hydrosilylation reactions with unprecedented activity and selectivity (TOF = 240 h(-1) at -40 degrees C, ee up to 99% for alkyl aryl ketones), which match the performance of previously established noble-metal-based catalysts. This shows the potential of earth-abundant metals such as iron for replacing platinum-metals without any drawbacks for the reaction design.
引用
收藏
页码:2456 / 2459
页数:4
相关论文
共 55 条
[1]   Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones [J].
Addis, Daniele ;
Shaikh, Nadim ;
Zhou, Shaolin ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthius .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) :1687-1691
[2]   Iron Hydride Complexes Bearing Phosphinite-Based Pincer Ligands: Synthesis, Reactivity, and Catalytic Application in Hydrosilylation Reactions [J].
Bhattacharya, Papri ;
Krause, Jeanette A. ;
Guan, Hairong .
ORGANOMETALLICS, 2011, 30 (17) :4720-4729
[3]   Electron-Rich N-Heterocyclic Silylene (NHSi)-Iron Complexes: Synthesis, Structures, and Catalytic Ability of an Isolable Hydridosilylene-Iron Complex [J].
Blom, Burgert ;
Enthaler, Stephan ;
Inoue, Shigeyoshi ;
Irran, Elisabeth ;
Driess, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (17) :6703-6713
[4]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[5]   A new iron age [J].
Bolm, Carsten .
NATURE CHEMISTRY, 2009, 1 (05) :420-420
[6]   ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH A CHIRAL TITANOCENE CATALYST [J].
CARTER, MB ;
SCHIOTT, B ;
GUTIERREZ, A ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :11667-11670
[7]   Radical Ligands Confer Nobility on Base-Metal Catalysts [J].
Chirik, Paul J. ;
Wieghardt, Karl .
SCIENCE, 2010, 327 (5967) :794-795
[8]   Asymmetric catalysis using iron complexes - 'Ruthenium Lite'? [J].
Darwish, Muftah ;
Wills, Martin .
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (02) :243-255
[9]   Anionic Chiral Tridentate N-Donor Pincer Ligands in Asymmetric Catalysis [J].
Deng, Qing-Hai ;
Melen, Rebecca L. ;
Gade, Lutz H. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (10) :3162-3173
[10]   Copper-Boxmi Complexes as Highly Enantioselective Catalysts for Electrophilic Trifluoromethylthiolations [J].
Deng, Qing-Hai ;
Rettenmeier, Christoph ;
Wadepohl, Hubert ;
Gade, Lutz H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (01) :93-97