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] COPPER(I) CATALYSIS IN CYCLOPROPANATIONS WITH DIAZO-COMPOUNDS - ROLE OF OLEFIN COORDINATION
    SALOMON, RG
    KOCHI, JK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) : 3300 - 3310
  • [2] Copper-homoscorpionate complexes as very active catalysts for the olefin aziridination reaction
    Mairena, MA
    Díaz-Requejo, MM
    Belderraín, TR
    Nicasio, MC
    Trofimenko, S
    Pérez, PJ
    ORGANOMETALLICS, 2004, 23 (02) : 253 - 256
  • [3] Organometallic complexes as catalysts for olefin polymerization
    Shen, HY
    Wang, X
    Jin, GX
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2003, 19 (09) : 913 - 919
  • [4] ZIRCONOCENE COMPLEXES AS OLEFIN HYDROSILATION CATALYSTS
    KESTI, M
    WAYMOUTH, RM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 423 - INOR
  • [5] OLEFIN AND ACETYLENE COMPLEXES OF DIVALENT COPPER
    ZELONKA, RA
    BAIRD, MC
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 33 (02) : 267 - &
  • [6] Copper-based olefin polymerization catalysts
    Stibrany, RT
    Patil, AO
    Zushma, S
    BEYOND METALLOCENES: NEXT GENERATION POLYMERIZATION CATALYSTS, 2003, 857 : 194 - 209
  • [7] Copper based olefin polymerization catalysts.
    Stibrany, RT
    Patil, AO
    Zushma, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : D66 - D66
  • [8] Vanadyl cationic complexes as catalysts in olefin oxidation
    Nunes, Carla D.
    Vaz, Pedro D.
    Felix, Vitor
    Veiros, Luis F.
    Moniz, Tania
    Rangel, Maria
    Realista, Sara
    Mourato, Ana C.
    Calhorda, Maria Jose
    DALTON TRANSACTIONS, 2015, 44 (11) : 5125 - 5138
  • [9] Metallacyclic metallocene complexes as catalysts for olefin polymerization
    Alt, HG
    Licht, EH
    Licht, AI
    Schneider, KJ
    COORDINATION CHEMISTRY REVIEWS, 2006, 250 (1-2) : 2 - 17
  • [10] Preface - Metallocene complexes as catalysts for olefin polymerization
    Alt, HG
    COORDINATION CHEMISTRY REVIEWS, 2006, 250 (1-2) : 1 - 1