Pd-catalyzed aerobic oxidative coupling of arenes: Evidence for transmetalation between two Pd(II)-aryl intermediates

Journal of the American Chemical Society

Volumn 136, Issue 28, 2014, Pages 9914-9917

  Wang, Dian ^a   Izawa, Yusuke ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CHEMICAL ACTIVATION; ISOTOPES; PALLADIUM COMPOUNDS;

BIARYL COMPOUNDS; C-H ACTIVATION; KINETIC ISOTOPE EFFECTS; KINETIC STUDY; OXIDATIVE COUPLINGS; REDUCTIVE ELIMINATION; TRANSMETALATION; TRIFLUOROACETATES;

CATALYSIS;

ISOTOPE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINE DERIVATIVE; TRIFLUOROACETIC ACID; AROMATIC HYDROCARBON; DEUTERIUM; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OXYGEN;

ARTICLE; CATALYST; COVALENT BOND; KINETICS; OXIDATIVE COUPLING; CATALYSIS; CHEMISTRY;

CATALYSIS; DEUTERIUM; HYDROCARBONS, AROMATIC; INDICATORS AND REAGENTS; KINETICS; OXYGEN; PALLADIUM; TRIFLUOROACETIC ACID;

EID: 84904438288     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja505405u     Document Type: Article

References (62)

1. Thompson, Q. E. Biphenyl and Terphenyls. In Kirk-Othmer Encyclopedia of Chemical Technology; Wiley: Hoboken, NJ, 2000; pp 1-13.
2. Mohri, Y. Seni Gakkaishi 1994, 50, 96
3. Kreuz, J. A.; Edman, J. R. Adv. Mater. 1998, 10, 1229
4. Takeoshi, T. Polyimides. In Advances in Polymer Science; Springer-Verlag: Berlin, Germany, 1990; Vol. 94, pp 2-22.
5. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
6. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540
9. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400
10. Itatani, H.; Yoshimoto, H.; Shiotani, A.; Yokota, A.; Yoshikiyo, M. U.S. Patent 4,294,976, 1981.
11. Izawa, Y.; Stahl, S. S. Adv. Synth. Catal. 2010, 352, 3223
12. van Helden, R.; Verberg, G. Recl. Trav. Chim. Pays-Bas 1965, 84, 1263
13. Davidson, J. M.; Triggs, C. J. Chem. Soc. A 1968, 1331
14. Yoshimoto, H.; Itatani, H. J. Catal. 1973, 31, 8
15. Iataaki, H.; Yoshimoto, H. J. Org. Chem. 1973, 38, 76
16. Stock, L. M.; Tse, K.-t.; Vorvick, L. J.; Walstrum, S. A. J. Org. Chem. 1981, 46, 1757
17. Itatani, H.; Shiotani, A.; Yokota, A. U.S. Patent 4,338,456, 1982.
18. Shiotani, A.; Itatani, H.; Inagaki, T. J. Mol. Catal. 1986, 34, 57
19. Mukhopadhyay, S.; Rothenberg, G.; Lando, G.; Agbaria, K.; Kazanci, M.; Sasson, Y. Adv. Synth. Catal. 2001, 343, 455
20. Yokota, T.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2002, 344, 849
21. Lee, S. H.; Lee, K. H.; Lee, J. S.; Jung, J. D.; Shim, J. S. J. Mol. Catal. A: Chem. 1997, 115, 241
22. Rong, Y.; Li, R.; Lu, W. Organometallics 2007, 26, 4376
23. Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047
24. Masui, K.; Ikegami, H.; Mori, A. J. Am. Chem. Soc. 2004, 126, 5074
25. Hartwig, J. F. Inorg. Chem. 2007, 46, 1936
26. Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031
27. Dedieu, A. Chem. Rev. 2000, 100, 543
28. Xue, L.; Lin, Z. Chem. Soc. Rev. 2010, 39, 1692
29. Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212
30. Popp, B. V.; Stahl, S. S. Chem.-Eur. J. 2009, 15, 2915
31. Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188
32. Muzart, J. Chem.-Asian J. 2006, 1, 508
33. Ryabov, A. D.; Sakodinskaya, I. K.; Yatsimirsky, A. K. J. Chem. Soc., Dalton Trans. 1985, 14, 2629
34. Karig, G.; Moon, M.-T.; Thasana, N.; Gallagher, T. Org. Lett. 2002, 4, 3115
35. García-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066
36. Ackermann, L. Chem. Rev. 2011, 111, 1315
37. Balcells, D.; Clot, E.; Eisenstein, O. Chem. Rev. 2010, 110, 749
38. Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172
39. Lyons, T. W.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 4455
40. Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115
41. Potavathri, S.; Dumas, A. S.; Dwight, T. A.; Naumiec, G. R.; Hammann, J. M.; DeBoef, B. Tetrahedron Lett. 2008, 49, 4050
42. Zhao, X.; Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 5837
43. Liu, B.; Huang, Y.; Lan, J.; Song, F.; You, J. Chem. Sci. 2013, 4, 2163
44. Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 9651
45. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 3308
46. Sun, H.-Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L.-C.; Fagnou, K. J. Org. Chem. 2010, 75, 8180
47. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848
48. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Org. Chem. 2012, 77, 658
49. Davidson, J. M.; Triggs, C. J. Chem. Soc. A 1968, 1324
50. Yatsimirsky, A. K.; Deiko, S. A.; Ryabov, A. D. Tetrahedron 1983, 39, 2381
51. Ackerman, L. J.; Sadighi, J. P.; Kurtz, D. M.; Labinger, J. A.; Bercaw, J. E. Organometallics 2003, 22, 3884
52. Lotz, M. D.; Remy, M. S.; Lao, D. B.; Ariafard, A.; Yates, B. F.; Canty, A. J.; Mayer, J. M.; Sanford, M. S. J. Am. Chem. Soc. 2014, 136, 8237
53. Ozawa, F.; Fujimori, M.; Yamamoto, T.; Yamamoto, A. Organometallics 1986, 5, 2144
54. Casado, A. L.; Caseras, J. A.; Espinet, P. Organometallics 1997, 16, 5730
55. Tan, Y.; Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 3683
56. See, for example, ref 16 and the following: Kashima, M.; Yoshimoto, H.; Itatani, H. J. Catal. 1973, 29, 92
57. Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072
58. Campbell, A. N.; Meyer, E. B.; Stahl, S. S. Chem. Commun. 2011, 47, 10257
59. Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084
60. Campeau, L. C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581
61. Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879
62. Geary, L. M.; Hultin, P. G. Eur. J. Org. Chem. 2010, 5563