Mechanistic studies of the oxidative dehydrogenation of methanol using a cationic palladium complex

Organometallics

Volumn 28, Issue 13, 2009, Pages 3896-3900

  Pearson, David M ^a   Waymouth, Robert M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; CATIONIC PALLADIUM COMPLEXES; HYDROGEN ELIMINATION; MECHANISTIC STUDIES; METHYL FORMATE; OXIDATION OF METHANOL; OXIDATIVE DEHYDROGENATIONS; TERMINAL OXIDANTS;

DEHYDROGENATION; FORMALDEHYDE; HYDROGEN; LABELS; METHANOL; PALLADIUM; PALLADIUM COMPOUNDS;

CATALYTIC OXIDATION;

EID: 67650337055     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900217s     Document Type: Article

References (46)

1. Carrette, L.; Friedrich, K. A.; stimming, U. ChemtPhysChem 2000, 1 (4), 162-193.
2. Hogarth, M. P.; Ralph, T. R. Plat. Met. Rev. 2002, 46 (4), 146-164.
3. Olah, G. A. Angew. Chem., Int. Ed. 2005, 44 (18), 2636-2639.
4. Beden, B.; Hahn, F.; Juanto, S.; Lamy, C.; Leger, J. M. J. Electroanal. Chem. 1987, 225 (1-2), 215-225.
5. Jusys, Z.; Kaiser, J.; Behm, R. J. Electrochim. Acta 2002, 47 (22-23), 3693-3706.
6. Burstein, G. T.; Barnett, C. J.; Kucernak, A. R.; Williams, K. R. Catal. Today 1997, 38 (4), 425-437.
7. Periana, R. A.; Mironov, O.; Taube, D.; Bhalla, G.; Jones, C. J. Science 2003, 301 (5634), 814-818.
8. Portnoy, M.; Milstein, D. Organometallics 1994, 13 (2), 600-609.
9. Conley, N. R.; Labios, L. A.; Pearson, D. M.; Mccrory, C.; Chidsey, C. E. D.; Waymouth, R. M. Organometallics 2007, 26 (23), 5447-5453.
10. Starchevsky, M. K.; Hladiy, S. L.; Pazdersky, Y. A.; Vargaftik, M. N.; Moiseev, 1.1. J. Mol. Catal. A: Chem. 1999, 146 (1-2), 229-236.
11. Lastovyak, Y. V.; Gladii, S. L.; Pasichnyk, P. I.; Starchevskii, M. K.; Pazderskii, Y. A.; Vargaftik, M. N.; Moiseev, I. I. Kinet. Catal. 1994, 35 (4), 512-515.
12. Lloyd, W. G. J. Org. Chem. 1967, 32 (9), 2816-2818.
13. Nishimura, T.; Kakiuchi, N.; Onoue, T.; Ohe, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 1915-1918.
14. Cant, N. W.; Tonner, S. P.; Trimm, D. L.; Wainwright, M. S. J. Catal. 1985, 91 (2), 197-207.
15. Iwasa, N.; Yamamoto, O.; Akazawa, T.; Ohyama, S.; Takezawa, N. J. Chem. Soc., Chem. Commun. 1991, 1322-1323.
16. Liu, Z.-T.; Lu, D.-S.; Guo, Z.-Y. Appl. Catal., A 1994, 118 (2), 163-171.
17. Forzatti, P.; Tronconi, E.; Busca, G.; Tittarelli, P. Catal. Today 1987, 1 (1-2), 209-218.
18. Miyazaki, E.; Yasumori, I. Bull. Chem. Soc. Jpn. 1967, 40 (9), 2012-2017.
19. Pocker, Y.; Davis, B. C. J. Chem. Soc., Chem. Commun. 1974, 803-804.
20. Ikarashi, T. Chem. Econ. Eng. Rev. 1980, 12 (8), 31-34.
21. Lee, J. S.; Kim, J. C.; Kim, Y. G. Appl. Catal. 1990, 57 (1), 1-30.
22. Roeper, M. Erdoel Kohle, Erdgas, Petrochem. 1984, 37 (11), 506-510.
23. Aguilo, A.; Horlenko, T. Hydrocarbon Process. 1980, 59 (11), 120.
24. Darensbourg, D. J.; Gray, R. L.; Ovalles, C.; Pala, M. J. Mol. Catal. 1985, 29 (2), 285-290.
25. Head, R. A.; Tabb, M. I. J. Mol. Catal. 1984, 26 (1), 149-158.
26. Inoue, Y.; Sasaki, Y.; Hashimoto, H. J. Chem. Soc., Chem. Commun. 1975, No. 17, 718-719.
27. Stahl, S. Angew. Chem., Int. Ed. 2004, 43 (26), 3400-3420.
28. Stoltz, B. M. Chem. Lett. 2004, 33 (4), 362-367.
29. Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229.
30. Schultz, M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227-8241.
31. Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344 (3-4), 355-369.
32. Arends, I.; Tenbrink, G.; Sheldon, R. J. Mol. Catal. A: Chem. 2006, 251 (1-2), 246-254.
33. Amatore, C.; Cammoun, C.; Jutand, A. Synlett 2007, No. 14, 2173-2178.
34. Grennberg, H.; Gogoll, A.; Baeckvall, J. Organometallics 1993, 12 (5), 1790-1793.
35. Baeckvall, J.; Bystroem, S.; Nordberg, R. J. Org. Chem. 1984, 49 (24), 4619-4631.
36. Baeckvall, J.; Hopkins, R.; Grennberg, H.; Mader, M.; Awasthi, A. J. Am. Chem. Soc. 1990, 112 (13), 5160-5166.
37. Popp, B. V.; Thorman, J. L.; Stahl, S. S. J. Mol. Catal. A: Chem. 2006, 251(1-2), 2-7.
38. Noronha, G.; Henry, P. M. J. Mol. Catal. A: Chem. 1997, 120 (1-3), 75-87.
39. 3.
40. 13C in these sources, we estimate 62 m/z should account for 1% of the total observable isotopes and conclude that the level observed is within our experimental error.
41. Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. J. Org. Chem. 2005, 70, 3343-3352.
42. Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755.
43. It is not clear if formaldehyde remains bound to Pd or if it is released into solution.
44. Reactions were run separately, and the isotope effect was estimated from the initial rates of methanol consumption.
45. Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124 (28), 8202-8203.
46. Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4 (23), 4179-4181.