Synthesis, characterization, and the role of counterion in cyclopropanation of styrene catalyzed by [CuI(2,2′-bpy)(π-CH2CHC6H5)][A] complexes
作者： Carolynne Ricardo , Tomislav Pintauer
DOI: 10.1016/J.JORGANCHEM.2007.07.045
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摘要: Abstract Copper(I)/2,2′-bipyridine complexes, [CuI(bpy)(π-CH2CHC6H5)][A] ( A = CF 3 SO - 1 ) , PF 6 2 have been synthesized and characterized. The equilibrium constants for the coordination of styrene to [CuI(bpy)]+ cations at 300 K were determined be 4.3 × 103 (1), 4.4 × 103 (2) 3.8 × 103 M−1 ClO 4 . These data suggested that axial counterion in these complexes observed solid state (2.4297(11) A 1, 2.9846(12) A 2, 2.591(4) A 3) did not significantly affect binding constant solution. In cyclopropanation reactions catalyzed by 1–3, similar product distribution was obtained. rate decomposition EDA presence room temperature (kobs = (7.7 ± 0.32) × 10−3 min−1) slower than (kobs = (1.4 ± 0.041) × 10−2 min−1) or (kobs = (1.0 ± 0.025) × 10−2 min−1).
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sci-hub.se 参考文章(44)
Andreas Pfaltz, Eric N. Jacobsen, 尚 山本, Comprehensive asymmetric catalysis Springer. ,(1999)
Humphrey John Moule Bowen, L. E. Sutton, Tables of interatomic distances and configuration in molecules and ions Chemical Society. ,(1958)
David A. Evans, Margaret M. Faul, Mark T. Bilodeau, Benjamin A. Anderson, David M. Barnes, Bis(oxazoline)-copper complexes as chiral catalysts for the enantioselective aziridination of olefins Journal of the American Chemical Society. ,vol. 115, pp. 5328- 5329 ,(1993) , 10.1021/JA00065A068
Erwan Galardon, Paul Le Maux, Loic Toupet, Gérard Simonneaux, SYNTHESIS, CRYSTAL STRUCTURE, AND REACTIVITY OF (5,10,15,20-TETRAPHENYLPORPHYRINATO)RUTHENIUM(II) (DIETHOXYCARBONYL)CARBENE METHANOL Organometallics. ,vol. 17, pp. 565- 569 ,(1998) , 10.1021/OM970790U
Pedro J. Perez, M. Brookhart, J. L. Templeton, A copper(I) catalyst for carbene and nitrene transfer to form cyclopropanes, cyclopropenes, and aziridines Organometallics. ,vol. 12, pp. 261- 262 ,(1993) , 10.1021/OM00026A007
Wade A. Braunecker, Tomislav Pintauer, Nicolay V. Tsarevsky, Guido Kickelbick, Krzysztof Matyjaszewski, Towards understanding monomer coordination in atom transfer radical polymerization: synthesis of [CuI(PMDETA)(π-M)][BPh4] (M = methyl acrylate, styrene, 1-octene, and methyl methacrylate) and structural studies by FT-IR and 1H NMR spectroscopy and X-ray crystallography Journal of Organometallic Chemistry. ,vol. 690, pp. 916- 924 ,(2005) , 10.1016/J.JORGANCHEM.2004.10.035
Michael P. Doyle, John H. Griffin, Vahid Bagheri, Roberta L. Dorow, Correlations between catalytic reactions of diazo compounds and stoichiometric reactions of transition-metal carbenes with alkenes. Mechanism of the cyclopropanation reaction Organometallics. ,vol. 3, pp. 53- 61 ,(1984) , 10.1021/OM00079A011
Xuliang Dai, Timothy H. Warren, Discrete Bridging and Terminal Copper Carbenes in Copper-Catalyzed Cyclopropanation Journal of the American Chemical Society. ,vol. 126, pp. 10085- 10094 ,(2004) , 10.1021/JA047935Q
Christopher G. Hamaker, Gholam A. Mirafzal, L. Keith Woo, Catalytic Cyclopropanation with Iron(II) Complexes Organometallics. ,vol. 20, pp. 5171- 5176 ,(2001) , 10.1021/OM010513U
Corey T. Cunningham, Jeffrey J. Moore, Kurstan L. H. Cunningham, Phillip E. Fanwick, David R. McMillin, Structural and photophysical studies of Cu(NN)2+ systems in the solid state. Emission at last from complexes with simple 1,10-phenanthroline ligands. Inorganic Chemistry. ,vol. 39, pp. 3638- 3644 ,(2000) , 10.1021/IC000082S