Non-heme iron catalysts for epoxidation and aziridination reactions of challenging terminal alkenes: towards sustainability

被引:100
|
作者
Fingerhut, Anja [1 ]
Serdyuk, Olga V.
Tsogoeva, Svetlana B.
机构
[1] Univ Erlangen Nurnberg, Organ Chem Chair 1, Dept Chem & Pharm, D-91054 Erlangen, Germany
关键词
NONHEME IRON; ASYMMETRIC EPOXIDATION; HYDROGEN-PEROXIDE; ENANTIOSELECTIVE EPOXIDATION; AROMATIC ALKENES; RING EXPANSION; COMPLEXES; OLEFINS; OXIDATION; H2O2;
D O I
10.1039/c4gc02413c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Through catalytic epoxidation and aziridination of olefins versatile synthetic intermediates and subunits of biologically active compounds and pharmaceuticals -epoxides and aziridines-can be obtained. The focus of this review is on recent advances in the epoxidation and aziridination of challenging terminal alkenes with respect to safety of solvents or reagents used and atom economy aspects, as well as scope and limitations of developed non-heme iron catalysts. The still large research potential for sustainable and environmentally attractive iron-based catalysts in enantioselective epoxide and aziridine synthesis is demonstrated.
引用
收藏
页码:2042 / 2058
页数:17
相关论文
共 50 条
  • [21] Speciation in iron epoxidation catalysis: A perspective on the discovery and role of non-heme iron(III)-hydroperoxo species in iron-catalyzed oxidation reactions
    Hoelzl, Sebastian M.
    Altmann, Philipp J.
    Kueck, Jens W.
    Kuehn, Fritz E.
    COORDINATION CHEMISTRY REVIEWS, 2017, 352 : 517 - 536
  • [22] Mechanistic investigation of non-heme iron-aminopyridine oxidation catalysts
    Piquette, Marc
    Makhlynets, Olga
    Bowen, Daniel
    Rybak-Akimova, Elena
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [23] New non-heme iron model compounds as catalysts in the oxidation of olefins
    de Laorden, CL
    Merz, M
    Comba, P
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2003, 96 (01) : 175 - 175
  • [24] Oxyfunctionalization of polystyrene by hydrogen peroxide using non-heme iron catalysts
    McArthur, Shelley
    Baird, Michael C.
    EUROPEAN POLYMER JOURNAL, 2014, 55 : 170 - 178
  • [25] Novel non-heme iron complexes as oxidation catalysts in alkene functionarlization
    Wada, A
    Ogo, S
    Watanabe, Y
    Jitsukawa, K
    Masuda, H
    Einaga, H
    JOURNAL OF INORGANIC BIOCHEMISTRY, 1999, 74 (1-4) : 331 - 331
  • [26] Mechanistic Investigation of a Non-Heme Iron Enzyme Catalyzed Epoxidation in (-)-4′-Methoxycyclopenin Biosynthesis
    Chang, Wei-chen
    Li, Jikun
    Lee, Justin L.
    Cronican, Andrea A.
    Guo, Yisong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (33) : 10390 - 10393
  • [27] Olefin cis-dihydroxylation versus epoxidation by non-heme iron catalysts:: Two faces of an FeIII-OOH coin
    Chen, K
    Costas, M
    Kim, JH
    Tipton, AK
    Que, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) : 3026 - 3035
  • [28] Non-Heme Imine-Based Iron Complexes as Catalysts for Oxidative Processes
    Olivo, Giorgio
    Lanzalunga, Osvaldo
    Di Stefano, Stefano
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (06) : 843 - 863
  • [29] Non-heme iron catalysts for the benzylic oxidation: a parallel ligand screening approach
    Klopstra, M
    Hage, R
    Kellogg, RM
    Feringa, BL
    TETRAHEDRON LETTERS, 2003, 44 (24) : 4581 - 4584
  • [30] A Non-Heme Iron(III) Complex with Porphyrin-like Properties That Catalyzes Asymmetric Epoxidation
    Niwa, Takashi
    Nakada, Masahisa
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13538 - 13541