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Pure Appl. Chem., 2009, Vol. 81, No. 7, pp. 1217-1227

http://dx.doi.org/10.1351/PAC-CON-08-10-08

Published online 2009-05-29

Scorpionate complexes of vanadium(III or IV) as catalyst precursors for solvent-free cyclohexane oxidation with dioxygen

Gopal S. Mishra1, Telma F. S. Silva2,1, Luísa M. D. R. S. Martins1,3 and Armando J. L. Pombeiro1*

1 Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, TU Lisbon, Av. Rovisco Pais, 1049-001, Lisbon, Portugal
2 Área Científica de Física, ISEL, R. Conselheiro Emídio Navarro, 1959-007, Lisbon, Portugal
3 Departamento de Engenharia Química, ISEL, R. Conselheiro Emídio Navarro, 1959-007, Lisbon, Portugal

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  • F. S. Silva Telma, M. D. R. S. Martins Luísa, Guedes da Silva M. Fátima C., Kuznetsov Maxim L., Fernandes Alexandra R., Silva Ana, Pan Chun-Jern, Lee Jyh-Fu, Hwang Bing-Joe, J. L. Pombeiro Armando: Cobalt Complexes with Pyrazole Ligands as Catalyst Precursors for the Peroxidative Oxidation of Cyclohexane: X-ray Absorption Spectroscopy Studies and Biological Applications. Chem. Asian J. 2014, 9, 1132. <http://dx.doi.org/10.1002/asia.201301331>
  • Martins Luísa M.D.R.S., Pombeiro Armando J.L.: Tris(pyrazol-1-yl)methane metal complexes for catalytic mild oxidative functionalizations of alkanes, alkenes and ketones. Coordination Chemistry Reviews 2014, 265, 74. <http://dx.doi.org/10.1016/j.ccr.2014.01.013>
  • Martins L. M. D. R. S., de Almeida M. Peixoto, Carabineiro S. A. C., Figueiredo J. L., Pombeiro A. J. L.: Heterogenisation of a C-Scorpionate FeII Complex on Carbon Materials for Cyclohexane Oxidation with Hydrogen Peroxide. ChemCatChem 2013, 5, 3847. <http://dx.doi.org/10.1002/cctc.201300432>
  • Gupta Samik, Kirillova Marina V., Guedes da Silva M. Fátima, Pombeiro Armando J.L.: Highly efficient divanadium(V) pre-catalyst for mild oxidation of liquid and gaseous alkanes. Applied Catalysis A: General 2013, 460-461, 82. <http://dx.doi.org/10.1016/j.apcata.2013.03.034>
  • Martins L.M.D.R.S., Martins A., Alegria E.C.B.A., Carvalho A.P., Pombeiro A.J.L.: Efficient cyclohexane oxidation with hydrogen peroxide catalysed by a C-scorpionate iron(II) complex immobilized on desilicated MOR zeolite. Applied Catalysis A: General 2013, 464-465, 43. <http://dx.doi.org/10.1016/j.apcata.2013.05.022>
  • Carabineiro S.A.C., Martins L.M.D.R.S., Avalos-Borja M., Buijnsters J.G., Pombeiro A.J.L., Figueiredo J.L.: Gold nanoparticles supported on carbon materials for cyclohexane oxidation with hydrogen peroxide. Applied Catalysis A: General 2013, 467, 279. <http://dx.doi.org/10.1016/j.apcata.2013.07.035>
  • Kirillov Alexander M., Shul’pin Georgiy B.: Pyrazinecarboxylic acid and analogs: Highly efficient co-catalysts in the metal-complex-catalyzed oxidation of organic compounds. Coordination Chemistry Reviews 2013, 257, 732. <http://dx.doi.org/10.1016/j.ccr.2012.09.012>
  • Mishra Gopal S., Machado Kelly, Kumar Anil: Highly selective n-alkanes oxidation to ketones with molecular oxygen catalyzed by SBA-15 supported rhenium catalysts. Journal of Industrial and Engineering Chemistry 2013. <http://dx.doi.org/10.1016/j.jiec.2013.09.055>
  • Silva Telma F.S., Leod Tatiana C.O. Mac, Martins Luísa M.D.R.S., Guedes da Silva M. Fátima C., Schiavon Marco A., Pombeiro Armando J.L.: Pyrazole or tris(pyrazolyl)ethanol oxo-vanadium(IV) complexes as homogeneous or supported catalysts for oxidation of cyclohexane under mild conditions. Journal of Molecular Catalysis A: Chemical 2013, 367, 52. <http://dx.doi.org/10.1016/j.molcata.2012.10.024>
  • Zhang Xiaoxi, Xing Na, Bai Fengying, Wan Lijuan, Shan Hui, Hou Yanan, Xing Yongheng, Shi Zhan: Multi-functional d10 metal–organic materials based on bis-pyrazole/pyridine ligands supported by a 2,6-di(3-pyrazolyl)pyridine with different spanning flexible dicarboxylate ligands: synthesis, structure, photoluminescent and catalytic properties. CrystEngComm 2013, 15, 9135. <http://dx.doi.org/10.1039/c3ce41213j>
  • de Almeida M. Peixoto, Martins L. M. D. R. S., Carabineiro S. A. C., Lauterbach T., Rominger F., Hashmi A. S. K., Pombeiro A. J. L., Figueiredo J. L.: Homogeneous and heterogenised new gold C-scorpionate complexes as catalysts for cyclohexane oxidation. Catal. Sci. Technol. 2013, 3, 3056. <http://dx.doi.org/10.1039/c3cy00552f>
  • Sutradhar Manas, Shvydkiy Nikita V., Guedes da Silva M. Fátima C., Kirillova Marina V., Kozlov Yuriy N., Pombeiro Armando J. L., Shul'pin Georgiy B.: A new binuclear oxovanadium(v) complex as a catalyst in combination with pyrazinecarboxylic acid (PCA) for efficient alkane oxygenation by H2O2. Dalton Trans. 2013, 42, 11791. <http://dx.doi.org/10.1039/c3dt50584g>
  • Milunovic Miljan N. M., Martins Luísa M. D. R. S., Alegria Elisabete C. B. A., Pombeiro Armando J. L., Krachler Regina, Trettenhahn Günter, Turta Constantin, Shova Sergiu, Arion Vladimir B.: Hexanuclear and undecanuclear iron(iii) carboxylates as catalyst precursors for cyclohexane oxidation. Dalton Trans. 2013, 42, 14388. <http://dx.doi.org/10.1039/c3dt50966d>
  • Shul'pin Georgiy B.: C–H functionalization: thoroughly tuning ligands at a metal ion, a chemist can greatly enhance catalyst's activity and selectivity. Dalton Trans. 2013, 42, 12794. <http://dx.doi.org/10.1039/c3dt51004b>
  • Shul'pin Georgiy B., Kozlov Yuriy N., Shul'pina Lidia S., Carvalho Wagner A., Mandelli Dalmo: Oxidation reactions catalyzed by osmium compounds. Part 4. Highly efficient oxidation of hydrocarbons and alcohols including glycerol by the H2O2/Os3(CO)12/pyridine reagent. RSC Adv. 2013, 3, 15065. <http://dx.doi.org/10.1039/c3ra41997e>
  • Rocha Bruno G.M., Wanke Riccardo, Guedes da Silva M. Fátima C., Luzyanin Konstantin V., Martins Luísa M.D.R.S., Smolénski Piotr, Pombeiro Armando J.L.: Reactivity of bulky tris(phenylpyrazolyl)methanesulfonate copper(I) complexes towards small unsaturated molecules. Journal of Organometallic Chemistry 2012, 714, 47. <http://dx.doi.org/10.1016/j.jorganchem.2012.03.022>
  • Wan Lijuan, Zhang Caishun, Xing Yongheng, Li Zhen, Xing Na, Wan Liying, Shan Hui: Neutral Mononuclear, Dinuclear, Tetranuclear d7/d10 Metal Complexes Containing bis-Pyrazole/Pyridine Ligands Supported by 2,6-bis(3-Pyrazolyl)Pyridine: Synthesis, Structure, Spectra, and Catalytic Activity. Inorg. Chem. 2012, 51, 6517. <http://dx.doi.org/10.1021/ic202678s>
  • Silva Telma F. S., Martins Luísa M. D. R. S., Guedes da Silva M. Fátima C., Fernandes Alexandra R., Silva Ana, Borralho Pedro M., Santos Susana, Rodrigues Cecília M. P., Pombeiro Armando J. L.: Cobalt complexes bearing scorpionate ligands: synthesis, characterization, cytotoxicity and DNA cleavage. Dalton Trans. 2012, 41, 12888. <http://dx.doi.org/10.1039/c2dt11577h>
  • Xing Na, Shan Hui, Zhao Hai-Yan, Xing Yong-Heng: Application in the cyclohexane oxidation of a scorpionate oxovanadium(IV) complex: synthesis, structure, and properties of VO(C5H7O2)(BC9H7N6I3). J  Coord Chem 2012, 65, 898. <http://dx.doi.org/10.1080/00958972.2012.661049>
  • Fernandes Ricardo R., Lasri Jamal, da Silva M. Fátima C. Guedes, da Silva José A.L., Fraústo da Silva João J.R., Pombeiro Armando J.L.: Mild alkane C–H and O–H oxidations catalysed by mixed-N,S copper, iron and vanadium systems. CATAL A GENERAL 2011, 402, 110. <http://dx.doi.org/10.1016/j.apcata.2011.05.035>
  • Silva Telma F.S., Guedes da Silva M. Fátima, Mishra Gopal S., Martins Luísa M.D.R.S., Pombeiro Armando J.L.: Synthesis and structural characterization of iron complexes with 2,2,2-tris(1-pyrazolyl)ethanol ligands: Application in the peroxidative oxidation of cyclohexane under mild conditions. J Organomet Chem 2011, 696, 1310. <http://dx.doi.org/10.1016/j.jorganchem.2010.12.036>
  • Fernandes Ricardo R., Lasri Jamal, Guedes da Silva M. Fátima C., da Silva José A.L., Fraústo da Silva João J.R., Pombeiro Armando J.L.: Bis- and tris-pyridyl amino and imino thioether Cu and Fe complexes. Thermal and microwave-assisted peroxidative oxidations of 1-phenylethanol and cyclohexane in the presence of various N-based additives. Journal of Molecular Catalysis A 2011, 351, 100. <http://dx.doi.org/10.1016/j.molcata.2011.09.022>
  • Marchetti Fabio, Pettinari Claudio, Pettinari Riccardo, Cerquetella Adele, Martins Luísa M. D. R. S., Guedes da Silva M. Fátima C., Silva Telma F. S., Pombeiro Armando J. L.: Ruthenium(II) Arene Complexes Bearing Tris(pyrazolyl)methanesulfonate Capping Ligands. Electrochemistry, Spectroscopic, and X-ray Structural Characterization. Organomettalics 2011, 30, 6180. <http://dx.doi.org/10.1021/om200713v>
  • Silva Telma F. S., Luzyanin Konstantin V., Kirillova Marina V., da Silva M. Fátima Guedes, Martins Luísa M. D. R. S., Pombeiro Armando J. L.: Novel Scorpionate and Pyrazole Dioxovanadium Complexes, Catalysts for Carboxylation and Peroxidative Oxidation of Alkanes. Adv Synth Catal 2010, 352, 171. <http://dx.doi.org/10.1002/adsc.200900660>
  • Dinoi Chiara, Guedes da Silva M. Fátima C., Alegria Elisabete C. B. A., Smoleński Piotr, Martins Luísa M. D. R. S., Poli Rinaldo, Pombeiro Armando J. L.: Molybdenum Complexes Bearing the Tris(1-pyrazolyl)methanesulfonate Ligand: Synthesis, Characterization and Electrochemical Behaviour. Euro J Inorg Chem 2010, 2010, 2415. <http://dx.doi.org/10.1002/ejic.201000018>
  • Silva Telma F. S., Mishra Gopal S., Guedes da Silva M. Fátima, Wanke Riccardo, Martins Luísa M. D. R. S., Pombeiro Armando J. L.: CuII complexes bearing the 2,2,2-tris(1-pyrazolyl)ethanol or 2,2,2-tris(1-pyrazolyl)ethyl methanesulfonate scorpionates. X-Ray structural characterization and application in the mild catalytic peroxidative oxidation of cyclohexane. Dalton Trans 2009, 9207. <http://dx.doi.org/10.1039/b911990f>