Mechanism of benzoquinone-promoted palladium-catalyzed oxidative cross-coupling reactions

Journal of the American Chemical Society

Volumn 131, Issue 28, 2009, Pages 9651-9653

  Hull, Kami L ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[H]QUINOLINE; BENZOQUINONE; CHEMICAL EQUATIONS; CHEMO-SELECTIVITY; CROSS COUPLING REACTIONS; CROSS-COUPLING; ELECTRONIC EFFECTS; H/D EXCHANGE; KINETIC ISOTOPE EFFECTS; MECHANISTIC STUDIES; RATIONAL TUNING; REACTION CONDITIONS;

CHEMICAL BONDS; CHEMICAL REACTIONS; ISOTOPES;

PALLADIUM;

BENZOQUINONE; ISOTOPE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT;

ARTICLE; ASSAY; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTRONICS; OXIDATION; STOICHIOMETRY;

EID: 67650495369     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja901952h     Document Type: Article

References (42)

1. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev 2002, 102, 1359.
2. Li, C. J. Acc. Chem. Res. 2009, 42, 335, and references therein.
3. For Pd-catalyzed homocoupling, see: (a) Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047.
4. (b) Mori, A.; Sugie, A. Bull. Chem. Soc. Jpn. 2008, 81, 548.
5. (c) Xia, J. B.; Wang, X. Q.; You, S. L. J. Org. Chem. 2009, 74, 456.
6. (d) Rong, Y.; Li, R.; Lu, W. Organometallics 2007, 26, 4376.
7. For stoichiometric Pd-mediated oxidative cross-coupling, see: (a) Itahara, T. Synthesis 1979, 151.
8. (b) Itahara, T.; Kawasaki, K.; Ouseto, F. Bull. Chem. Soc. Jpn. 1984, 57, 3488.
9. (c) Itahara, T. J. Org. Chem. 1985, 50, 5272.
10. (a) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
11. (b) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
12. (c) Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072.
13. (d) Potavathri, S.; Dumas, A. S.; Dwight, T. A.; Naumiec, G. R.; Hammann, J. M.; DeBoef, B. Tetrahedron Lett. 2008, 49, 4050.
14. (e) Fagnou, K.; Liegault, B. Organometallics 2008, 27, 4841.
15. (f) Liegault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022.
16. Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904.
17. (a) Xia, J.; You, S. Organometallics 2007, 26, 4869.
18. (b) Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666.
19. (c) Brasche, G.; Garcia-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207.
20. Li, R.; Jiang, L.; Lu, W. Organometallics 2006, 25, 5973.
21. II(BQ) complexes are extremely rare in the literature (see ref 12c), presumably because they are highly reactive towards reductive elimination. See: (a) Pérez-Rodríguez, M.; Braga, A. A. C.; Garcia-Melchor, M.; Pérez-Temprano, M. H.; Casares, J. A.; Ujaque, G.; de Lera, A. R.; Alvarez, R.; Maseras, F.; Espinet, P. J. Am. Chem. Soc. 2009, 131, 3650.
22. (b) Szabo, K. J. Organometallics 1998, 17, 1677.
23. DMSO (4 equiv) was added in each of the mechanistic experiments for consistency with the catalytic reactions (ref 6). Order studies revealed that the reaction is zeroth-order with respect to this additive (see the Supporting Information for details).
24. The control reaction in the absence of Pd showed <1% D incorporation.
25. II is well-precedented. For examples, see ref 9 and: (a) Temple, J. S.; Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 1310.
26. (b) Backvall, J. E.; Bystrom, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
27. (c) Albeniz, A. C.; Espinet, P.; Martin-Ruiz, B. Chem. - Eur. J. 2001, 7, 2481.
28. (d) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
29. (e) Chen, X.; Li, J.; Hao, X.; Goodhue, C. E.; Yu, J. J. Am. Chem. Soc. 2006, 128, 78.
30. Analysis of the crude reaction mixture did not show the presence of any hydroquinone, suggesting that the BQ plays a non-redox role in this transformation. The major Pd-containing product appears to be Pd black, which precipitates from solution over the course of the C-C coupling.
31. (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
32. (b) Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A 1996, 108, 35.
33. (c) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
34. (d) Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285.
35. (a) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
36. (b) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
37. (c) Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848.
38. (a) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
39. (b) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
40. (c) Park, C. H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
41. For calculations describing a related mechanism, see: Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754.
42. Similar effects were observed in the catalytic reaction (using AgOAc as a stoichiometric oxidant). With 0.25 equiv of BQ, 10/9 = 1.45:1, while with 25 equiv of BQ, 10/9 = 1:1.2. This suggests that these stoichiometric mechanistic studies are relevant and applicable to the catalytic transformation.