Silver-catalyzed C-C bond formation between methane and ethyl diazoacetate in supercritical CO2

Science

Volumn 332, Issue 6031, 2011, Pages 835-838

  Caballero, Ana ^a   Despagnet Ayoub, Emmanuelle ^b,c   Díaz Requejo, M Mar ^a   Díaz Rodríguez, Alba ^a,d   González Núñez, María Elena ^d   Mello, Rossella ^d   Muñoz, Bianca K ^b,c   Ojo, Wilfried Solo ^b,c   Asensio, Gregorio ^d   Etienne, Michel ^b,c   Pérez, Pedro J ^a  

^a UNIVERSITY OF HUELVA   (Spain)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^c UNIVERSITÉ DE TOULOUSE   (France)

^d UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; CARBON DIOXIDE; DIAZOACETIC ACID ETHYL ESTER; METHANE; PERFLUORO COMPOUND; PROPIONIC ACID DERIVATIVE; PROPIONIC ACID ETHYL ESTER; SILVER; UNCLASSIFIED DRUG;

CARBON DIOXIDE; CATALYSIS; ESTER; METHANE; OPTIMIZATION; ORGANIC COMPOUND; SILVER; SOLVENT; VOLATILIZATION;

ARTICLE; CATALYSIS; CHEMICAL BOND; CONTROLLED STUDY; PRIORITY JOURNAL;

EID: 79956011526     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1204131     Document Type: Article

References (36)

1. R. H. Crabtree, Chem. Rev. 110, 575 (2010).
2. R. G. Bergman, Nature 446, 391 (2007).
3. J. A. Labinger, J. E. Bercaw, Nature 417, 507 (2002).
4. K. I. Goldberg, A. S. Goldman, Eds., Activation and Functionalization of C-H Bonds [American Chemical Society (ACS) Symposium Series 885, ACS, Washington, DC, 2004].
5. B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Petersen, Acc. Chem. Res. 28, 154 (1995).
6. J. F. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, (University Science Books, Sausalito, CA, 2009).
7. J. T. Golden, R. A. Andersen, R. G. Bergman, J. Am. Chem. Soc. 123, 5837 (2001).
8. C. M. Jensen, Chem. Commun. 1999, 2443 (1999).
9. A. S. Goldman et al., Science 312, 257 (2006).
10. A. D. Sadow, T. D. Tilley, J. Am. Chem. Soc. 127, 643 (2005).
11. I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 110, 890 (2010).
12. A. E. Shilov, G. B. Shul'pin, Chem. Rev. 97, 2879 (1997).
13. R. A. Periana et al., Science 259, 340 (1993).
14. R. A. Periana et al., Science 280, 560 (1998).
15. C. J. Jones et al., Angew. Chem. Int. Ed. 43, 4626 (2004).
16. R. A. Periana, O. Mironov, D. J. Taube, G. Bhalla, C. J. Jones, Science 301, 814 (2003).
17. M. V. Kirillova et al., J. Am. Chem. Soc. 129, 10531 (2007).
18. G. A. Olah, Acc. Chem. Res. 20, 422 (1987).
19. G. A. Olah, A. Molnar, in Hydrocarbon Chemistry (Wiley-Interscience, Hoboken, NJ, ed. 2, 2003), chap. 9, pp. 427-575.
20. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 110, 704 (2010).
21. M. M. Díaz-Requejo, T. R. Belderraín, M. C. Nicasio, P. J. Pérez, Dalton Trans. 2006, 5559 (2006).
22. H. M. L. Davies, T. Hansen, M. R. J. Churchill, J. Am. Chem. Soc. 122, 3063 (2000).
23. H.-Y. Thu et al., Angew. Chem. Int. Ed. 47, 9747 (2008).
24. M. M. Díaz-Requejo, P. J. Pérez, Chem. Rev. 108, 3379 (2008).
25. J. Urbano et al., Organometallics 24, 1528 (2005).
26. E. Despagnet-Ayoub et al., Organometallics 27, 4779 (2008).
27. J. Urbano et al., Organometallics 28, 5968 (2009).
28. J. M. DeSimone, E. Tumas, Eds., Green Chemistry Using Liquid and Supercritical Carbon Dioxide (Oxford Univ. Press, Oxford, 2003).
29. Materials and methods are available as supporting material on Science Online.
30. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds (Wiley, New York, 1998).
31. A. Caballero, A. Prieto, M. M. Diaz-Requejo, P. J. Pérez, Eur. J. Inorg. Chem. 2009, 1137 (2009).
32. S. J. Blanksby, G. B. Ellison, Acc. Chem. Res. 36, 255 (2003).
33. E. Nakamura, N. Yoshikai, M. Yamanaka, J. Am. Chem. Soc. 124, 7181 (2002).
34. A. A. C. Braga et al., Organometallics 25, 5292 (2006).
35. A reviewer mentioned the possibility of the involvement of radical species. Extensive previous work favors the metallocarbene route [see (19) and references therein]. Moreover, these experiments were carried out in a vessel that was neither purged nor vented; therefore, 100 mL of air was present in the reaction mixture. The oxygen contained in that volume would preclude the conversion of any radical into the desired product. See (36).
36. G. Asensio, R. Mello, M. E. González-Núñez, C. Boix, J. Royo, Tetrahedron Lett. 38, 2373 (1997).