Галогенидные комплексы циркония. Синтез, строение, возможности практического применения

Автор: Шарутин Владимир Викторович, Тарасова Наталья Михайловна

Журнал: Вестник Южно-Уральского государственного университета. Серия: Химия @vestnik-susu-chemistry

Рубрика: Химия элементоорганических соединений

Статья в выпуске: 1 т.15, 2023 года.

Бесплатный доступ

На основе анализа литературы, опубликованной преимущественно с 2018 по 2021 г., систематизированы и описаны методы получения, некоторые реакции, особенности строения галогенидных комплексов циркония и примеры их возможного использования. При обсуждении методов синтеза основное внимание уделено наиболее эффективным подходам к их получению. Рассмотрены реакции образования комплексных соединений циркония. Приведены сведения о биологической и каталитической активности некоторых производных циркония.

Синтез, строение, галогенидные комплексы циркония

Короткий адрес: https://sciup.org/147239553

IDR: 147239553   |   DOI: 10.14529/chem230102

Список литературы Галогенидные комплексы циркония. Синтез, строение, возможности практического применения

  • Джемилев У.М., Вострикова О.С., Ибрагимов А.Г. Комплексы циркония в синтезе и катализе // Успехи химии. 1986. Т. 2. С. 191-224. DOI: 10.1070/RC1986v055n02ABEH003172.
  • Schwartz I., Labinger J. Hydrozirconation: A new transition metal reagent for organic synthesis // Angew. Chem. Int. Ed. Engl. 1976. Vol. 15. P. 333-340. DOI: 10.1002/anie.197603331.
  • Schwartz J. Organozirconium compounds in organic synthesis: cleavage reactions of carbon-zirconium bonds // Pure Appl. Chem. 1980. Vol. 52. P. 733-740. DOI: 10.1351/pac198052030733.
  • Rogers J.S., Bazan G.C., Sperry C.K. Ethoxyboratabenzene zirconium complexes: catalysts for a-olefin production // J. Am. Chem. Soc. 1997. Vol. 119. P. 9305-9306. DOI: 10.1021/ja971976n.
  • Novel zirconium complexes with constrained cyclic ß-enaminoketonato ligands: improved catalytic capability toward ethylene polymerization / K.-T. Wang, Y.-X. Wang, B. Wang et al. // Dalton Trans. 2016. Vol. 45. P. 10308-10318. DOI: 10.1039/C6DT01391K.
  • Zirconium enolatoimine complexes in olefinpolymerization / S.M. Yu, U. Tritschler, I. Göttker-Schnetmann et al. // Dalton Trans. 2010. Vol. 39. P. 4612-4618. DOI: 10.1039/B916289E.
  • Titanium and zirconium permethylpentalene complexes, Pn*MCpRX, as ethylene polymerization catalysts / D A X. Fraser, Z.R. Turner, J.-Ch. Buffet et al. // Organometallics. 2016. Vol. 35. P. 26642674. DOI: 10.1021/acs.organomet.6b00417.
  • Highly active and isospecific styrene polymerization catalyzed by zirconium complexes bearing aryl-substituted [OSSO]-type bis(phenolate) ligands / N. Nakata, T. Toda, Y. Saito et al. // Polymers. 2016. Vol. 8. P. 31. DOI: 10.3390/polym8020031.
  • Theaker G.W., Morton C., Scott P. Zirconium-catalyzed polymerization of a styrene: catalyst reactivation mechanisms using alkenes and dihydrogen // Macromolecules. 2011. Vol. 44. P. 13931404. DOI: 10.1021/ma102835p.
  • Catalytically active N-acylamidine-zirconium complexes: synthesis, structures, and application in ethylene polymerization / Th. Holtrichter-Rößmann, I. Häger, C.-G. Daniliuc et al. // Organometallics. 2016. Vol. 35. P. 1906-1915. DOI: 10.1021/ acs.organomet.6b00240.
  • Kerr R.W.F., Williams Ch.K. Zr(IV) catalyst for the ring-opening copolymerization of anhydrides (A) with epoxides (B), oxetane (B), and tetrahydrofurans (C) to make ABB- and/or ABC-poly(ester-alt-ethers) // J. Am. Chem. Soc. 2022. Vol. 144, no. 15, P. 6882-6893. DOI: 10.1021/jacs.2c01225.
  • Cuenca T., Flores J.C., Royo P. Dicyclopentadienyl-titanium and -zirconium complexes as catalysts for hydrogenation of olefins // J. Organomet. Chem. 1993. Vol. 462. P. 191-201. DOI: 10.1016/0022- 328X(93)83357-2.
  • Stoichiometric Reactions and catalytic hydrogenation with a reactive intramolecular Zr+/amine frustrated Lewis pair / X. Xu, G. Kehr, C.G. Daniliuc et al. // J. Am. Chem. Soc. 2015. Vol. 137. P. 4550-4557. DOI: 10.1021/jacs.5b01623.
  • Highly enantioselective Friedel-Crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes / G. Blay, I. Fernández, J.R. Pedro et al. // Org. Lett. 2007. Vol. 9. P. 2601-2604. DOI: 10.1021/ol0710820.
  • Enantioselective zirconium-catalyzed Friedel-Crafts alkylation of pyrrole with trifluoromethyl ketones / G. Blay, I. Fernandez, A. Monleon et al. // Org. Lett. 2009. Vol. 11. P. 441-444. DOI: 10.1021/ol802509m.
  • Mo L.-P., Zhang Zh.-H. Recent applications of zirconium compounds as catalysts or reagents in organic synthesis // Curr. Org. Chem. 2011. Vol. 15. P. 3800-3823. DOI: 10.2174/138527211797884520.
  • Machine-learning-assisted synthesis of polar racemates / M.L. Nisbet, I.M. Pendleton, G.M. Nolis et al. // J. Am. Chem. Soc. 2020. Vol. 142. P. 7555-7566. DOI: 10.1021/jacs.0c01239.
  • [Na-15-Krone-5]2[ZrF2Cl4] und (PPh4)2[ZrCl6] • 2CH2Cl2; Synthesen, IR-spektren und kristallstrukturen / [Na-15-Crown-5]2[ZrF2Cl4] and (PPh4)2[ZrCl6] • 2CH2Cl2; Syntheses, IR Spectra, and crystal structures / E. Hartmann, K. Dehnicke, D. Fenske et al. // Z. Naturforsch., B: Chem. Sci. 1989. Vol. 44. P. 1155-1160. DOI: 10.1515/znb-1989-1001.
  • Chen L., Cotton F.A. Synthesis, structure, and reactivity of [Zr6Cli8H5]2-, the first paramagnetic species of its class // Inorg. Chem. 1996. Vol. 35. P. 7364-7369. DOI: 10.1021/ic960454q.
  • Chen L., Cotton F.A., Wojtczak W.F. Synthesis and structural characterization of compounds containing the [Zr6Cli8H5]3- cluster anion. Determination of the number of cluster hydrogen atoms // Inorg. Chem. 1997. Vol. 36. P. 4047-4054. DOI: 10.1021/ic960173i.
  • Synthesis and structure of (Ph4P)2MCl6 (M = Ti, Zr, Hf, Th, U, Np, Pu) / Minasian S.G., Boland K.S., Feller R.K. et al. // Inorg. Chem. 2012. V. 51. P. 5728-5736. DOI: 10.1021/ic300179d
  • Gauch F., Strahle J. Synthese und kristallstrukturen der mehrker-nigen rhenium-nitrido-komplexe [Re2N2Cl4(PMe2Ph)4(MeCN)] und [Re^C^PMe.Ph^] // Z. Anorg. Allg. Chem. 2000. Vol. 626. P. 1153-1158. DOI: 10.1002/(SICI)1521-3749(200005)626:5< 1153: AID-ZAAC1153-3.0.CO;2-0.
  • Шарутин В.В., Шарутина О.К., Лобанова Е.В. Синтез и строение комплексов циркония [Ph3PR]+2[ZrCl6]2- (R = Et, CH2Ph, CH2C(O)OMe) // Журн. неорг. химии. 2018. Т. 63, № 12. С. 1549-1554. DOI: 10.1134/S0044457X1812019X
  • Синтез и строение комплексов циркония [Et2H2N]+2[ZrCl6]2-, [Me3NCH2Ph]+2[ZrCl6]2--MeCN, [Ph3PC6H4(CHPh2-4)]+2[ZrCy2--2MECN и ^Sbf^ZrCy2-'// В.В. Шарутин, О.К. Шарутина, Н.М. Тарасова и др. // Изв. АН. Сер. хим. 2019. № 1. С. 24-31.
  • Синтез и строение гексахлорцирконатов трифенилбут-2-енил и трифенилметоксиметил-фосфония. В.В. Шарутин, О.К. Шарутина, Н.М. Тарасова и др. // Изв. вузов. Химия и хим. технология. 2019. Т. 62, № 6. С. 36-40. DOI: 10.6060/ivkkt.20196206.5885
  • Синтез и строение гексахлорцирконата (4-фторбензил)трифенилфосфония [Ph3PCH2C6H4F-4][ZrCl6] / В.В. Шарутин, О.К. Шарутина, А.В. Рыбакова и др. // Вестник ЮжноУральского государственного университета. Серия «Химия». 2022. Т. 14, № 2. С. 90-97. DOI: 10.14529/chem220210.
  • Андреев П.В., Лобанова Е.В., Дрожилкин П.Д. Синтез и строение комплексов циркония [Ph3PCH=CHMe]2[ZrCl6] и гафния [Ph3PCH2C(O)Me]2[HfCl6] // Вестник ЮУрГУ. Серия «Химия». 2019. Т. 11, № 26. С. 26-33. DOI: 10.14529/chem190403.
  • Шарутин В.В., Шарутина О.К., Лобанова Е.В. Синтез и строение комплексов гафния [Ph3PR]+2[HfCl6]2-, R = Et, CH2C6H4CN-4, CH2C6H4F-4 // Журн. неорган. химии. 2020. Т. 65, № 6. С. 804-808. DOI: 10.31857/S0044457X2006020329.
  • Mixed transition metal(oxy)fluoride paramagnet chains: synthesis, structure, and characterization/ B.A. Ahmed, H. Jo, S.W. Yoon et al. // Eur. J. Inorg. Chem. 2019. Vol. 2019. P. 3112-3118. DOI: 10.1002/ejic.201900509
  • Separation of Xe from Kr with record selectivity and productivity in anion-pillared ultramicro-porous materials by inverse size-sieving / Q. Wang, T. Ke, Z. Zhang et al. // Angew. Chem., Int. Ed., 2020. Vol. 59. P. 3423-3428. DOI: 10.1002/anie.201913245.
  • Enhancing easy-plane anisotropy in bespoke Ni(II) quantum magnets / J.L. Manson, Z.E. Man-son, A. Sargent et al. // Polyhedron. 2020. Vol. 180. P. 114379. DOI: 10.1016/j.poly.2020.114379
  • Ahmed B., Jo H., Ok K.M. Variable chains found in mixed transition metal oxyfluorides with heterocyclic ligands // Cryst. Growth Des. 2019. Vol. 19, no. 6. P. 3435-3444. DOI: 10.1021/acs.cgd.9b00307.
  • Efficient Sr-90 removal from highly alkaline solution by an ultrastable crystalline zirconium phosphorate / J. Zhang, L. Chen, X. Dai et al. // Chem. Commun. 2021. Vol. 57, no. 68. P. 8452-8455. DOI: 10.1039/D1CC02446A.
  • Oxyphosphoranes as precursors to bridging phosphate-catecholate ligands / X. Yang, R. Wei, Y. Shi et al. // Chem. Commun. 2021. Vol. 57. P. 1194-1197. DOI: 10.1039/d0cc07736d
  • Cooperative metal-ligand hydroamination catalysis supported by C-H activation in cyclam Zr(IV) complexes / L.G. Alves, F. Madeira, R.F. Munhâ et al. // Inorg. Chem. 2018. Vol. 57. P. 1303413045. DOI: 10.1021/acs.inorgchem.8b02396.
  • Rahimi N., Herbert D.E., Budzelaar H.M. Formation and rearrangement of reduced diiminepy-ridine complexes of Zr and Hf // Eur. J. Inorg. Chem. 2018. Vol. 45. P. 4856-4866. DOI: 10.1002/ejic.201800918.
  • Photochemical synthesis of a zirconium cyclobutadienyl complex / P.M.N. Do, N.G. Akhmedov, J.L. Petersen et al. // Chem. Commun. 2020. Vol. 56. P. 5397-5400. DOI: 10.1039/D0CC01104E.
  • Arrested disproportionation in trivalent, mononuclear, and non-metallocene complexes of Zr(III) and Hf(III) / L.N. Grant, M.E. Miehlich, K. Meyer et al. // Chem. Commun. 2018. Vol. 54. P. 2052-2055. DOI: 10.1039/C7CC08815A.
  • Chen X., Gamer M.T., Roesky P.W. Synthesis and structural characterization of arsinoamides -early transition metal (Zr and Hf) and main group metal (Al, In, Sn, and Pb) complexes // Dalton Trans. 2019. Vol. 48, no. 40. P. 15207-15211. DOI: 10.1039/C9DT03472B.
  • Synthesis and structural characterization of zirconium complexes supported by tridentate pyrro-lide-imino ligands with pendant N-, O- and S-donor groups and their application in ethylene polymerization / A C. Pinheiro, S.M. da Silva, T. Roisnel et al. // New J. Chem. 2018. Vol. 42. P. 1477-1483. DOI: 10.1039/C7NJ04074A.
  • Asymmetric bis-PNP pincer complexes of zirconium and hafnium - a measure of hemilability / C. Idelson, L. Webster, T. Krämer et al. // Dalton Trans. 2020. Vol. 49. P. 16653-16656. DOI: 10.1039/D0DT03544K.
  • Nelsen M.J., Girolami G.S. Zirconium alkyls with ancillary cyclooctatetraenyl ligands. X-ray crystal structures of [Li(tmed)][(C8H8)Zr(p-C6H4Me)Cl2] and (C8H8)Zr[CH(SiMe3)2]2 // Polyhedron. 2020. Vol. 187. P. 114581. DOI: 10.1016/j.poly.2020.114581.
  • Unexpected precatalyst o-ligand effects in phenoxyimine Zr-catalyzed ethylene/1-octene copo-lymerizations / Y. Gao, M.D. Christianson, Y. Wang et al. // J. Am. Chem. Soc. 2019. Vol. 141. P. 7822-7830. DOI: 10.1021/jacs.9b01445.
  • Group 4 organometallics supported by sterically hindered ß-diketonates / E.J. Hopkins, S.M. Krajewski, A.S. Crossman et al. // Eur. J. Inorg. Chem. 2020. P. 1951-1959. DOI: 10.1002/ejic.202000135.
  • Titanium and zirconium complexes bearing new tridentate [OSO] bisphenolato-based ligands: synthesis, characterization and catalytic properties for alkene polymerization / T. Song, J. He, L. Liang et al. // Dalton Trans. 2019. Vol. 48. P. 13719-13731. DOI: 10.1039/C9DT03225H.
  • Cooperative H2 activation across a metal-metal multiple bond and hydrogenation reactions catalyzed by a Zr/Co heterobimetallic complex / K.M. Gramigna, D.A. Dickie, B.M. Foxman et al. // ACD Catalysis. 2019. Vol. 9. P. 3153-3164. DOI: 10.1021/acscatal.8b04390.
  • Avisar S., Bogoslavsky B., Bino A. Fusion of ferric citrate and zirconium hexafluoride: Synthesis, structure and magnetic properties of [Fe6O2Zr2F6(cit)4(H2O)i0] // Inorg Chim. Acta. 2018. Vol. 479. P. 161-164. DOI: 10.1016/j.ica.2018.04.012.
  • Neutral and anionic monomeric zirconium imides prepared via selective C=N bond cleavage of a multidentate and sterically demanding ß-diketiminato ligand / T. Kurogi, J. Chu, Y. Chen et al. // Chem. Asian J. 2019. Vol. 14. P. 2629-2638. DOI: 10.1002/asia.201900451.
  • Early metal di(piridyl) pyrrolide complexes with second coordination sphere Aren-л interaction: ligand binding and ethylene polymerization / J. Sampson, G. Choi, M.N. Akhtar et al. // ACD Omega. 2019. Vol. 4. P. 15879-15892. DOI: 10.1021/acsomega.9b01788.
  • Reappraising Schmidpeter's bis(iminophosphoranyl)phosphides: coordination to transition metals and bonding analysis / A.T. Normand, E.D.S. Carrizo, C. Magnoux et al. // Chem. Sci. 2021. Vol. 12. P. 253-269. DOI: 10.1039/D0SC04736H.
  • Alkyl substituents triggered an unexpected formation of mono-and dinuclear zirconium hydra-zonate complexes: synthesis, characterization and their catalytic behavior toward ethylene polymerization / X.-E. Duan, B. Yuan, R. Li et al. // Appl. Organomet. Chem. 2020. Vol. 34. P. e5586. DOI: 10.1002/aoc.5586.
  • A tunable trifluoromethyliodonium reagent / P. Liebing, J. Kalim, N. Arefyeva et al. // Angew. Chem. Int. Ed. Engl. 2019. Vol. 58. P. 8585-8588. DOI: 10.1002/anie.201903623.
  • Synthesis and reactivity of titanium- and zirconium-dinitrogen complexes bearing anionic pyrrole-based PNP-type pincer ligands / Y. Sekiguchi, F. Meng, H. Tanaka et al. // Dalton Trans. 2018. Vol. 47. P. 11322-11326. DOI: 10.1039/C8DT02739K.
  • Structural diversity in substituted aminosilyl-aminopyridinate metal (Zr or Fe) complexes: Synthesis, structures, and ethylene polymerization / X.-E. Duan, X.-X. Zhang, T. Liu et al. // Appl. Organomet. Chem. 2021. Vol. 35. P. e6240. DOI: 10.1002/aoc.6240.
  • Thompson R.R., Zavalij P.Y., Sita L.R. Electronic effect rate enhancement in the stereoselective living coordinative polymerization of a-olefins by a,a,a-trifluoroacetamidinate-modified group 4 metal CPAMCF3 initiators // Organometallics. 2018. Vol. 38. P. 213-217. DOI: 10.1021/acs.organomet.8b00839.
  • Рыбакова А.В. Синтез и строение хлорида циклопентадиенилдиферроценоилацетонато-циркония C5H5[C10H9FeC(O)CHC(O)CF3]2ZrCl // Вестник ЮУрГУ. Серия «Химия». 2021. Т. 13, № 2. С. 39-48. DOI: 10.14529/chem210204.
  • Синтез смешанных клешнеобразных циклопентадиенильных соединений циркония / Р.Х. Фрейдлина, Э.М. Брайнина и др. // Докл. АН СССР. 1961. Т. 138. С. 1369-1373.
  • Luminescent cationic group 4 metallocene complexes stabilized by pendant N-donor groups / D. Dunlop, M. Vecera, R. Gyepes et al. // Inorg. Chem. 2021. Vol. 60. P. 7315-7328. DOI: 10.1021/acs.inorgchem.1c00461.
  • Synthesis of zirconocene complexes and their use in slurry-phase polymerisation of ethylene / P. Angpanitcharoen, J.V. Lamb, J.-C. Buffet et al. // RSC Advances. 2021. Vol. 11. P. 11529-11535. DOI: 10.1039/D1RA01912K.
  • Multisubstituted C2-symmetric ansa-metallocenes bearing nitrogen heterocycles: influence of substituents on catalytic properties in propylene polymerization at higher temperatures / P.S. Kulyabin, V.V. Izmer, G.P. Goryunov et al. // Dalton Trans. 2021. Vol. 50. P. 6170-6180. DOI: 10.1039/D1DT00645B.
  • Synthesis and olefin polymerization performance of new ansa-zirconocene with OSiO-bridged 6/s(2-indenyl) ligand / I.S. Borisov, D.Yu. Mladentsev, et al. // Mendeleev Commun. 2020. Vol. 30. P. 449-452. DOI: 10.1016/j.mencom.2020.07.014.
  • Synthesis and olefin polymerization performance of new ansa-zirconocene with OSiO-bridged bis(2-indenyl) ligand / I.S. Borisov, D.Yu. Mladentsev et al. // Mendeleev Commun. 2020. Vol. 30. P. 449-452. DOI: 10.1016/j.mencom.2020.07.014.
  • Ring-opening polymerisation of l- and rac-lactide using group 4 permethylpentalene aryloxides and alkoxides / Z.R. Turner, J.V. Lamb, T P. Robinson et al. // Dalton Trans. 2021. Vol. 50. P. 48054818. DOI: 10.1039/D1DT00252J.
Еще
Статья научная