Tris(pyrazol-1-yl)methane metal complexes for catalytic mild oxidative functionalizations of alkanes, alkenes and ketones

Coordination Chemistry Reviews

Volumn 265, Issue 1, 2014, Pages 74-88

  Martins, Luísa M D R S ^a,b   Pombeiro, Armando J L ^b  

^a INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

C scorpionate; Homogeneous catalysis; Oxidation; Oxidative functionalization; Supported catalysis; Tris(pyrazol 1 yl)methane

Indexed keywords

EID: 84893514810     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2014.01.013     Document Type: Review

References (85)

1. Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 6th ed.
2. Whyman R. Applied Organometallic Chemistry and Catalysis 2001, Oxford University Press, Oxford.
3. Smiley R.A., Jackson H.L. Chemistry and the Chemical Industry 2002, CRC Press, Boca Raton, FL.
4. Weissermel K., Arpe H.-J. Industrial Organic Chemistry 1993, VCH Press, Weinheim. 2nd ed.
5. Bäckvall J.-E. Modern Oxidation Methods 2004, Wiley-VCH, Weinheim.
6. Sheldon R.A., Arends I., Hanefeld U. Green Chemistry and Catalysis 2007, Wiley-VCH, Weinheim.
7. Metal-catalysis in Industrial Organic Processes 2006, Royal Society of Chemistry, Cambridge, (Chapter 2, 4). G.P. Chiusoli, P.M. Maitlis (Eds.).
8. Pettinari C. Scorpionates II: Chelating Borate Ligands 2008, Imperial College Press, World Scientific Pub, London.
9. Trofimenko S., Scorpionates: The Coordination Chemistry of Polypyrazolylborates Ligands 1999, Imperial College Press, London.
10. Pettinari C., Santini C. Comprehensive Coordination Chemistry II: From Biology to Nanotechnology 2003, vol. 1:159. Elsevier Pergamon (APS), Amsterdam.
11. Pettinari C., Pettinari R. Coord. Chem. Rev. 2005, 249:525.
12. Bigmore H.R., Lawrence C.S., Mountford P., Tredget C.S. Dalton Trans. 2005, 635.
13. Otero A., Fernández-Baeza J., Lara-Sánchez A., Sánchez-Barba L.F. Coord. Chem. Rev. 2013, 257:1806.
14. Shul'pin G.B. Mini-rev. Org. Chem. 2009, 6:95.
15. Catalytic Activation and Functionalization of Light Alkanes, NATO ASI Series 1998, vol. 44. Kluwer Academic Publishers, Dordrecht, The Netherlands.
16. Activation and Functionalization of Alkanes 1989, Wiley, New York. C.L. Hill (Ed.).
17. Methane Conversion by Oxidative Processes: Fundamental and Engineering Aspects 1992, Van Nostrand Reinhold, New York. E.E. Wolf (Ed.).
18. Shilov A.E., Shul'pin G.B. Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes 2000, Kluwer Academic Publishers, Dordrecht, The Netherlands.
19. Jia C.G., Kitamura T., Fujiwara Y. Acc. Chem. Rev. 2001, 34:633.
20. Crabtree R.H. J. Chem. Soc., Dalton Trans. 2001, 2437.
21. Shul'pin G.B. C.R. Chimie 2003, 6:163.
22. da Silva J.A.L., Fraústo da Silva J.J.R., Pombeiro A.J.L. Coord. Chem. Rev. 2011, 255:2232.
23. Pombeiro A.J.L. Vanadium: The Versatile Metal, ACS Symposium Series 974 2007, 51. American Chemical Society, Washington, DC. K. Kustin, J.C. Pessoa, D.C. Crans (Eds.).
24. Shul'pin G.B. Dalton Trans. 2013, 42:12794.
25. Kirillov A.M., Kirillova M.V., Pombeiro A.J.L. Coord. Chem. Rev. 2012, 256:2741.
26. Michelin R.A., Sgarbossa P., Scarso A., Strukul G. Coord. Chem. Rev. 2010, 254:646.
27. ten Brink G.-J., Arends I.W.C.E., Sheldon R.A. Chem. Rev. 2004, 104:4105.
28. Seiser T., Saget T., Tran D.N., Cramer N. Angew. Chem. Int. Ed. 2011, 50:7740.
29. Jin P., Zhu L., Wei D., Tang M., Wang X. Comput. Theor. Chem. 2011, 966:207.
30. Silva T.F.S., Luzyanin K.V., Kirilova M.V., Silva M.F.C., Martins L.M.D.R.S., Pombeiro A.J.L. Adv. Synth. Catal. 2010, 352:171.
31. Silva T.F.S., Mac Leod T.C.O., Martins L.M.D.R.S., Guedes da Silva M.F.C., Pombeiro A.J.L. J. Mol. Catal. A: Chem. 2013, 367:52.
32. Silva T.F.S., Alegria E.C.B.A., Martins L.M.D.R.S., Pombeiro A.J.L. Adv. Synth. Catal. 2008, 350:706.
33. Alegria E.C.B.A., Kirillova M.V., Martins L.M.D.R.S., Pombeiro A.J.L. Appl. Catal. A: Gen. 2007, 357:43.
34. Almeida M.P., 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. Catal. Sci. Technol. 2013, 3:3056.
35. Silva T.F.S., Mishra G.S., Silva M.F.C.G., Wanke R., Martins L.M.D.R.S., Pombeiro A.J.L. Dalton Trans. 2009, 9207.
36. Silva T.F.S., Silva M.F.C.G., Mishra G.S., Martins L.M.D.R.S., Pombeiro A.J.L. J. Organomet. Chem. 2011, 696:1350.
37. Shul'pin G.B. J. Mol. Catal. A: Chem. 2002, 189:39.
38. Shul'pin G.B., Kozlov Y.N., Shul'pina L.S., Kudinov A.R., Mandelli D. Inorg. Chem. 2009, 48:10480.
39. Shul'pin G.B., Kozlov Y.N., Shul'pina L.S., Petrovskiy P.V. Appl. Organomet. Chem. 2010, 24:464.
40. Kopylovich M.N., Kirillov A.M., Baev A.K., Pombeiro A.J.L. J. Mol. Catal. A: Chem. 2003, 206:163.
41. Fernandes R.R., Kirillova M.V., Silva J.A.L., Fraústo da Silva J.J.R., Pombeiro A.J.L. Appl. Catal. A 2009, 353:107.
42. Kirillova M.V., Kirillov A.M., Guedes da Silva M.F.C., Pombeiro A.J.L. Eur. J. Inorg. Chem. 2008, 3423.
43. Shul'pin G.B., Gradinaru J., Kozlov Y.N. Org. Biomol. Chem. 2003, 1:3611.
44. Kirillov A.M., Kopylovich M.N., Kirillova M.V., Karabach E.Y., Haukka M., da Silva M.F.C.G., Pombeiro A.J.L. Adv. Synth. Catal. 2006, 348:159.
45. Kirillov A.M., Kopylovich M.N., Kirillova M.V., Haukka M., Guedes da Silva M.F.C., Pombeiro A.J.L. Angew. Chem., Int. Ed. 2005, 44:4345.
46. Di Nicola C., Karabach Y.Y., Kirillov A.M., Monari M., Pandolfo L., Pettinari C., Pombeiro A.J.L. Inorg. Chem. 2007, 46:221.
47. Di Nicola C., Garau F., Karabach Y.Y., Martins L.M.D.R.S., Monari M., Pandolfo L., Pettinari C., Pombeiro A.J.L. Eur. J. Inorg. Chem. 2009, 666.
48. Contaldi S., Di Nicola C., Garau F., Karabach Y.Y., Martins L.M.D.R.S., Monari M., Pandolfo L., Pettinari C., Pombeiro A.J.L. Dalton Trans. 2009, 4928.
49. Canhota F.P., Salomão G.C., Carvalho N.M.F., Antunes O.A.C. Catal. Commun. 2008, 9:182.
50. Howard J.A. Free Radicals 1973, 3. Wiley, New York. J.K. Kochi (Ed.).
51. Huie R.E., Clifton C.L. Int. J. Chem. Kinet. 1989, 21:611.
52. Slaughter L.M., Collman J.P., Eberspacher T.A., Brauman J.I. Inorg. Chem. 2004, 43:5198.
53. Kirillova M.V., Kuznetsov M.L., Romakh V.B., Shul'pina L.S., Fraústo da Silva J.J.R., Pombeiro A.J.L., Shul'pin G.B. J. Catal. 2009, 267:140.
54. Kirillova M.V., Kuznetsov M.L., Kozlov Y.N., Shul'pina L.S., Kitaygorodskiy A., Pombeiro A.J.L., Shul'pin G.B. ACS Catal. 2011, 1:1511.
55. Kuznetsov M.L., Pombeiro A.J.L. Inorg. Chem. 2009, 48:307.
56. Kirillova M.V., Kozlov Y.N., Shul'pina L.S., Lyakin O.Y., Kirillov A.M., Talsi E.P., Pombeiro A.J.L., Shul'pin G.B. J. Catal. 2009, 268:26.
57. Shul'pin G.B., Süss-Fink G. J. Chem. Soc. Perkin Trans. 1995, 2:1459.
58. Costas M., Chen K., Que L. Coord. Chem. Rev. 2000, 200-202:517.
59. Costas M., Mehn M.P., Jensen M.P., Que L. Chem. Rev. 2004, 104:939.
60. Company A., Gómez L., Güell M., Ribas X., Luis J.M., Que L., Costas M. J. Am. Chem. Soc. 2007, 129:15766.
61. England J., Britovsek G.J.P., Rabadia N., White A.J.P. Inorg. Chem. 2007, 46:3752.
62. Mishra G.S., Silva T.F.S., Martins L.M.D.R.S., Pombeiro A.J.L. Pure Appl. Chem. 2009, 81:1217.
63. Kirillov A.M., Shul'pin G.B. Coord. Chem. Rev. 2013, 257:732.
64. Kirillova M.V., Kuznetsov M.L., Reis P.M., Silva J.A.L., Fraústo da Silva J.J.R., Pombeiro A.J.L. J. Am. Chem. Soc. 2007, 129:10531.
65. Kirillova M.V., Kuznetsov M.L., Silva J.A.L., Guedes da Silva M.F.C., Fraústo da Silva J.J.R., Pombeiro A.J.L. Chem. Eur. J. 2008, 14:1828.
66. Asadullah M., Kitamura T., Fujiwara Y. Angew. Chem. 2000, 112:2609.
67. Asadullah M., Kitamura T., Fujiwara Y. Angew. Chem. Int. Ed. 2000, 39:2475.
68. Minisci F., Citterio A., Giordano G. Acc. Chem. Res. 1983, 16:27.
69. Yamaguchi M., Iida T., Yamagishi T. Inorg. Chem. Commun. 1998, 1:299.
70. Yamaguchi M., Tomizawa M., Takagaki K., Shimo M., Masui D., Yamagishi T. Catal. Today 2006, 117:206.
71. Martins L.M.D.R.S., Martins A., Alegria E.C.B.A., Carvalho A.P., Pombeiro A.J.L. Appl. Catal. A: Gen. 2013, 464-465:43.
72. Mishra G.S., Alegria E.C.B.A., Martins L.M.D.R.S., Fraústo da Silva J.J.R., Pombeiro A.J.L. J. Mol. Catal. A: Chem. 2008, 285:92.
73. Martins L.M.D.R.S., Almeida M.P., Carabineiro S.A.C., Figueiredo J.L., Pombeiro A.J.L. ChemCatChem 2013, 5:3847.
74. Kirillova M.V., Kirillov A.M., Reis P.M., Silva J.A.L., Fraústo da Silva J.J.R., Pombeiro A.J.L. J. Catal. 2007, 248:130.
75. Santos A.M., Kuhn F.E., Bruus-Jensen K., Lucas I., Romão C.C., Herdtweck E. J. Chem. Soc., Dalton Trans. 2001, 1332.
76. Neves P., Gago S., Balula S.S., Lopes A.D., Valente A.A., Cunha-Silva L., Paz F.A.A., Pillinger M., Rocha J., Silva C.M., Gonçalves I.S. Inorg. Chem. 2011, 50:3490.
77. Gomes A.C., Neves P., Figueiredo S., Fernandes J.A., Valente A.A., Paz F.A.A., Pillinger M., Lopes A.D., Gonçalves I.S. J. Mol. Catal. A: Chem. 2013, 370:64.
78. Agarwala H., Ehret F., Chowdhury A.D., Maji S., Mobin S.M., Kaim W., Lahiri G.K. Dalton Trans. 2013, 42:3721.
79. Alegria E.C.B., Martins L.M.D.R.S., Kirillova M.V., Pombeiro A.J.L. Appl. Catal. A: Gen. 2012, 443-444:27.
80. Martins L.M.D.R.S., Alegria E.C.B.A., Smoleński P., Kuznetsov M.L., Pombeiro A.J.L. Inorg. Chem. 2013, 52:4534.
81. Bernini R., Coratti A., Fabrezi G., Goggiamani A. Tetrahedron Lett. 2003, 44:8991.
82. Sgarbossa P., Guedes da Silva M.F.C., Scarso A., Michelin R.A., Pombeiro A.J.L. Inorg. Chim. Acta 2008, 361:3247.
83. Greggio G., Sgarbossa P., Scarso A., Michelin R.A., Strukul G. Inorg. Chim. Acta 2008, 361:3230.
84. Sgarbossa P., Scarso A., Pizzo E., Sbovata A.M., Tassan A., Michelin R.A., Strukul G. J. Mol. Catal. A 2007, 261:202.
85. Yoshida M., Masaoka S., Abe J., Sakai K. Chem. Asian J. 2010, 5:2369.