Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations

被引:30
作者
Youssef, Nabil S. [3 ]
El-Seidy, Ahmed M. A. [3 ]
Schiavoni, Marco [1 ,2 ]
Castano, Brunilde [1 ,2 ]
Ragaini, Fabio [1 ,2 ]
Gallo, Emma [1 ,2 ]
Caselli, Alessandro [1 ,2 ]
机构
[1] Univ Milan, Dipartimento Chim, I-20133 Milan, Italy
[2] CNR, ISTM, I-20133 Milan, Italy
[3] Natl Res Ctr, Dept Inorgan Chem, Giza, Egypt
关键词
Schiff bases; Copper complexes; Cyclopropanation reactions; Homogeneous catalysis; Thiosemicarbazone; ASYMMETRIC CYCLOPROPANATION; METAL-COMPLEXES; ENANTIOSELECTIVE CYCLOPROPANATION; SPECTROSCOPIC CHARACTERIZATION; CRYSTAL-STRUCTURE; CU(I) COMPLEXES; DIAZO-COMPOUNDS; LIGANDS; COORDINATION; ALKENES;
D O I
10.1016/j.jorganchem.2012.03.018
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New copper complexes of several thiosemicarbazones have been prepared and characterized. All complexes have been prepared by employing Cu (II) acetate hydrate, but analytical and spectroscopical data for the isolated complexes revealed that in most cases a reduction to copper (I) occurred. Cyclopropanation reactions of several olefins by ethyldiazoacetate (EDA) in the presence of catalytic amounts of the complexes were examined. The reported results showed that all complexes are competent catalysts for the cyclopropanation reaction of unactivated olefins. Cyclopropanes were obtained in high yields (up to 97%, TON up to 18,400) with moderate to excellent diastereoselectivities (up to >99%). (C) 2012 Elsevier B. V. All rights reserved.
引用
收藏
页码:94 / 103
页数:10
相关论文
共 50 条
  • [1] Synthesis and Characterization of New Schiff Base Metal Complexes and Their Use as Catalysts for Olefin Cyclopropanation
    Youssef, Nabil S.
    El-Zahany, Eman A.
    El-Seidy, Ahmed M. A.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (04) : 785 - 798
  • [2] Formation and Reactivity of Copper Acetylacetone Bis(Thiosemicarbazone) Complexes
    Bilyj, Jessica K.
    Harmer, Jeffery R.
    Bernhardt, Paul V.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (43) : 4731 - 4741
  • [3] Synthesis and characterization of some transition metal complexes with a novel Schiff base ligand and their use as catalysts for olefin cyclopropanation
    Youssef, Nabil S.
    El-Zahany, Eman
    El-Seidy, Ahmed M. A.
    Caselli, Alessandro
    Cenini, Sergio
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2009, 308 (1-2) : 159 - 168
  • [4] Synthesis and characterisation of new Schiff base metal complexes and their use as catalysts for olefin cyclopropanation
    Youssef, Nabil S.
    El-Zahany, Eman
    El-Seidy, Ahmed M. A.
    Caselli, Alessandro
    Fantauzzi, Simone
    Cenini, Sergio
    INORGANICA CHIMICA ACTA, 2009, 362 (06) : 2006 - 2014
  • [5] Palladium(II) carboxylates and palladium(I) carbonyl carboxylate complexes as catalysts for olefin cyclopropanation with ethyl diazoacetate
    Shishilov, Oleg N.
    Stromnova, Tatiana A.
    Campora, Juan
    Palma, Pilar
    Angeles Cartes, M.
    Miguel Martinez-Prieto, Luis
    DALTON TRANSACTIONS, 2009, (33) : 6626 - 6633
  • [6] Designing "Totem' C2-Symmetrical Iron Porphyrin Catalysts for Stereoselective Cyclopropanations
    Carminati, Daniela Maria
    Intrieri, Daniela
    Caselli, Alessandro
    Le Gac, Stephane
    Boitrel, Bernard
    Toma, Lucio
    Legnani, Laura
    Gallo, Emma
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (38) : 13599 - 13612
  • [7] Copper(I)-imine complexes: Synthesis and catalytic activity in olefin cyclopropanation
    Ardizzoia, G. Attilio
    Brenna, Stefano
    Castelli, Fulvio
    Galli, Simona
    INORGANICA CHIMICA ACTA, 2009, 362 (10) : 3507 - 3512
  • [8] Polyoxometalates: Powerful Catalysts for Atom-Efficient Cyclopropanations
    Boldini, Irene
    Guillemot, Geoffroy
    Caselli, Alessandro
    Proust, Anna
    Gallo, Emma
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2365 - 2370
  • [9] Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes
    Zhou, You-Yun
    Uyeda, Christopher
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (09) : 3171 - 3175
  • [10] Synthesis, structure, and cytotoxicity of complexes of zinc(II), palladium(II), and copper(I) chlorides with (-)-camphor thiosemicarbazone
    Kokina, Tatyana E.
    Glinskaya, Ludmila A.
    Sheludyakova, Liliya A.
    Eremina, Yuliya A.
    Klyushova, Lubov S.
    Komarov, Vladislav Yu
    Piryazev, Dmitriy A.
    Tkachev, Alexey, V
    Larionov, Stanislav, V
    POLYHEDRON, 2019, 163 : 121 - 130