Catalytic functionalization of methane and light alkanes in supercritical carbon dioxide

Chemistry - A European Journal

Volumn 20, Issue 35, 2014, Pages 11013-11018

  Fuentes, M Ángeles ^a   Olmos, Andrea ^a   Muñoz, Bianca K ^b,c   Jacob, Kane ^b,c   González Núñez, M Elena ^d   Mello, Rossella ^d   Asensio, Gregorio ^d   Caballero, Ana ^a   Etienne, Michel ^b,c   Pérez, Pedro J ^a  

^a UNIVERSITY OF HUELVA   (Spain)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^c UNIVERSITÉ PAUL SABATIER   (France)

^d UNIVERSITY OF VALENCIA   (Spain)

Author keywords

C H activation; carbene insertion; diazo compounds; methane activation; silver catalysts

Indexed keywords

ACTIVATION ANALYSIS; CARBON DIOXIDE; CATALYSIS; CATALYSTS; CHEMICAL ACTIVATION; SUPERCRITICAL FLUID EXTRACTION;

C-H ACTIVATION; CARBENE INSERTION; DIAZO COMPOUNDS; METHANE ACTIVATION; SILVER CATALYST;

METHANE;

EID: 84906785640     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403217     Document Type: Article

References (30)

1. V. N. Cavaliere, D. N. Mindiola, Chem. Sci. 2012, 3, 3356-3365.
2. A. V. Milkov, Earth-Sci. Rev. 2004, 66, 183-197.
3. H.-J. Arpe, Industrial Organic Chemistry, 5th ed., Wiley-VCH, 2010.
4. A. Caballero, P. J. Pérez, Chem. Soc. Rev. 2013, 42, 8809-8820.
5. A. E. Shilov, G. B. Shulpin, Chem. Rev. 1997, 97, 2879-2932.
6. R. A. Periana, D. J. Taube, E. R. Evitt, D. G. Löffler, P. R. Wentrcek, G. Voss, T. Masuda, Science 1993, 259, 340-343.
7. R. A. Periana, D. J. Taube, S. Gamble, H. Taube, T. Satoh, H. Fujii, Science 1998, 280, 560-563.
8. B. G. Hashiguchi, M. M. Konnick, S. M. Bischof, S. J. Gustafson, D. Devarajan, N. Gunsalus, D. H. Ess, R. A. Periana, Science 2014, 343, 1232-1237.
9. E. Gretz, T. F. Oliver, A. Sen, J. Am. Chem. Soc. 1987, 109, 8109-8111.
10. M. Muehlhofer, T. Strassner, W. A. Herrmann, Angew. Chem. 2002, 114, 1817-1819
11. Angew. Chem. Int. Ed. 2002, 41, 1745-1747.
12. M. V. Kirillova, M. L. Kuznetsov, P. M. Reis, J. A. L. da Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, J. Am. Chem. Soc. 2007, 129, 10531-10545.
13. R. A. Periana, O. Mironov, D. Taube, G. Bhalla, C. J. Jones, Science 2003, 301, 814-818.
14. P. J. Pérez, Alkane C-H Activation by Single-Site Metal Catalysis, Springer, 2012.
15. Y.-R. Luo, Comprehensive Handbook of Chemical Bond Energies, CRC, 2007.
16. M. Hackett, G. M. Whitesides, J. Am. Chem. Soc. 1988, 110, 1449-1462
17. H. Chen, J. F. Hartwig, Science 2000, 287, 1995-1997.
18. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, 1998.
19. See reference [13], Chapter 6, Alkane catalytic functionalization by carbene or nitrene insertion reactions, by M. M. Díaz-Requejo, A. Caballero, M. R. Fructos, P. J. Pérez.
20. K. P. Kornecki, J. F. Briones, V. Boyarskikh, F. Fullilove, J. Autschbach, K. E. Schrote, K. M. Lancaster, H. M. L. Davies, J. F. Berry, Science 2013, 342, 351-354.
21. H. M. L. Davies, A. R. Dick, Top. Curr. Chem. 2009, 292, 303-345.
22. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704-724.
23. A preliminary report related to this work has been published:, A. Caballero, E. Despagnet-Ayoub, M. M. Díaz-Requejo, A. Díaz-Rodríguez, M. E. González-Núñez, R. Mello, B. K. Muñoz, W. Solo Ojo, G. Asensio, M. Etienne, P. J. Pérez, Science 2011, 332, 835-838.
24. M. A. Fuentes, B. K. Muñoz, K. Jacob, L. Vendier, A. Caballero, M. Etienne, P. J. Pérez, Chem. Eur. J. 2013, 19, 1327-1334.
25. J. A. Gladysz, D. P. Curran, I. T. Horváth, Handbook of Fluorous Chemistry, Wiley-VCH, Weinheim, 2004.
26. These compounds are classified as nonclassical metal-carbonyls, since the ν(CO) frequency lies above that of free CO. For the first example of these complexes with a silver center, see:, P. K. Hurlburt, J. J. Rack, J. S. Luck, S. F. Dec, J. D. Webb, O. P. Anderson, S. H. Strauss, J. Am. Chem. Soc. 1994, 116, 10003-10014.
27. A. Caballero, M. M. Díaz-Requejo, S. Trofimenko, T. R. Belderraín, P. J. Pérez, Eur. J. Inorg. Chem. 2007, 2848-2852.
28. J. A. Flores, K. Nobuyuki, K. Pal, N. Pinter, M. Pink, C.-H. Chen, K. G. Caulton, D. N. Mindiola, ACS Catal. 2012, 2, 2066-2078.
29. E. Despagnet-Ayoub, K. Jacob, L. Vendier, M. Etienne, E. Álvarez, A. Caballero, M. M. Díaz-Requejo, P. J. Pérez, Organometallics 2008, 27, 4779-4787.
30. B. K. Muñoz, W.-S. Ojo, K. Jacob, N. Romero, L. Vendier, E. Despagnet-Ayoub, M. Etienne, New J. Chem. 2014, 38, 2451-2461.