New Catalysts for the Transition-Metal-Catalyzed Synthesis of Aziridines

被引:67
作者
Jung, Nicole [2 ]
Braese, Stefan [1 ]
机构
[1] Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] Inst Toxikol & Genet ITG, D-76344 Eggenstein Leopoldshafen, Germany
关键词
azides; aziridine synthesis; homogeneous catalysis; porphyrinoids; transition metals; ARYL AZIDES; ALKENES; OLEFINS; PORPHYRIN;
D O I
10.1002/anie.201200966
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
C 2+N 1: The transition-metal-catalyzed reaction of alkenes with azides is an important tool for the formation of aziridines. Besides many recently published ruthenium, copper, and manganese catalysts, a novel macrocyclic tetracarbene iron(II) catalyst promotes the synthesis of aziridines in good yields and with low catalyst loadings. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5538 / 5540
页数:3
相关论文
共 34 条
[1]   High-valent iron and manganese complexes of corrole and porphyrin in atom transfer and dioxygen evolving catalysis [J].
Abu-Omar, Mahdi M. .
DALTON TRANSACTIONS, 2011, 40 (14) :3435-3444
[2]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[3]  
Brase S., 2005, ANGEW CHEM, V117, P5320, DOI DOI 10.1002/ANGE.200400657
[4]   Catalytic amination of unsaturated hydrocarbons:: reactions of p-nitrophenylazide with alkenes catalysed by metallo-porphyrins [J].
Cenini, S ;
Tollari, S ;
Penoni, A ;
Cereda, C .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 137 (1-3) :135-146
[5]   Transition-metal-catalyzed aminations and aziridinations of C-H and C=C bonds with iminoiodinanes [J].
Chang, Joyce Wei Wei ;
Ton, Thi My Uyen ;
Chan, Philip Wai Hong .
CHEMICAL RECORD, 2011, 11 (06) :331-357
[6]   The mechanism of the (bispidine)copper(II)-catalyzed aziridination of styrene: A combined experimental and theoretical study [J].
Comba, Peter ;
Lang, Carolin ;
de Laorden, Carlos Lopez ;
Muruganantham, Amsaveni ;
Rajaraman, Gopalan ;
Wadepold, Hubert ;
Zajaczkowski, Marta .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (17) :5313-5328
[7]   Synthesis, Structure, and Highly Efficient Copper-Catalyzed Aziridination with a Tetraaza-Bispidine Ligand [J].
Comba, Peter ;
Haaf, Christina ;
Lienke, Achim ;
Muruganantham, Amsaveni ;
Wadepohl, Hubert .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (41) :10880-10887
[8]   Synthesis of Aziridines from Alkenes and Aryl Azides with a Reusable Macrocyclic Tetracarbene Iron Catalyst [J].
Cramer, S. Alan ;
Jenkins, David M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (48) :19342-19345
[9]   COPPER-CATALYZED AZIRIDINATION OF OLEFINS BY (N-(PARA-TOLUENESULFONYL)IMINO)PHENYLIODINANE [J].
EVANS, DA ;
FAUL, MM ;
BILODEAU, MT .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6744-6746
[10]   Origin of the deactivation in styrene aziridination by aryl azides, catalyzed by ruthenium porphyrin complexes.: Structural characterization of a Δ2-1,2,3-triazoline RuII(TPP)CO complex [J].
Fantauzzi, S ;
Gallo, E ;
Caselli, A ;
Ragaini, F ;
Macchi, P ;
Casati, N ;
Cenini, S .
ORGANOMETALLICS, 2005, 24 (20) :4710-4713