Aerobic oxidative coupling of o-xylene: Discovery of 2-fluoropyridine as a ligand to support selective Pd-catalyzed C-H functionalization

Advanced Synthesis and Catalysis

Volumn 352, Issue 18, 2010, Pages 3223-3229

  Izawa, Yusuke ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

aerobic oxidation; C H activation; industrial chemistry; oxidation; oxidative coupling; palladium

Indexed keywords

EID: 78650392932     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000771     Document Type: Article

References (64)

1. For leading references, see
2. Y. Rong, R. Li, W. Lu, Organometallics 2007, 26, 4376-4378
3. K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 14047-14049
4. S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501
5. Angew. Chem. Int. Ed. 2004, 43, 3400-3420
6. T. Yokota, S. Sakaguchi, Y. Ishii, Adv. Synth. Catal. 2002, 344, 849-854
7. S. Mukhopadhyay, G. Rothenberg, G. Lando, K. Agbaria, M. Kananci, Y. Sasson, Adv. Synth. Catal. 2001, 343, 455-459
8. A. V. Iretskii, S. C. Sherman, M. G. White, J. C. Kenvin, D. A. Schiraldi, J. Catal. 2000, 193, 49-57
9. S. H. Lee, K. H. Lee, J. S. Lee, J. D. Jung, J. S. Shim, J. Mol. Catal. B 1997, 115, 241-246
10. M. Okamoto, T. Yamaji, Chem. Lett. 2001, 212-213.
11. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172-1175
12. D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 12072-12073
13. B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131-1134
14. Angew. Chem. Int. Ed. 2008, 47, 1115-1118
15. G. Brasche, J. Garcia-Fortanet, S. L. Buchwald, Org. Lett. 2008, 10, 2207-2210
16. K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 11904-11905
17. T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137-3139
18. S. Potavathri, A. S. Dumas, T. A. Dwight, G. R. Naumiec, J. M. Hammann, B. DeBoef, Tetrahedron Lett. 2008, 49, 4050-4053
19. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254-9256
20. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, J. You, J. Am. Chem. Soc. 2010, 132, 1882-1884.
21. R. van Helden, G. Verberg, Recl. Trav. Chim. Pays-Bas 1965, 84, 1263-1273.
22. J. M. Davidson, C. Triggs, Chem. Ind. 1966, 457
23. J. M. Davidson, C. Triggs, Chem. Ind. 1967, 1361
24. J. M. Davidson, C. Triggs, J. Chem. Soc. (A) 1968, 1324-1330.
25. This process is currently used by Ube industries Ltd. For representative pantents, see
26. H. Itatani, M. Kashima, T. M. Matsuda, H. Yoshimoto, H. Yamamoto, U.S. Patent 3,940,426, 1976
27. H. Itatani, H. Yoshimoto, A. Shiotani, A. Yokota, M, Yoshikiyo, U.S. Patent 4,294,976, 1981
28. H. Itatani, A. Shiotani, A. Yokota, Japanese Patent 33379, 1985.
29. An efficient catalyst for dimethyl o-phthalate was reported. See
30. H. Iataaki, H. Yoshimoto, J. Org. Chem. 1973, 38, 76-79
31. H. Yoshimoto, H. Itatani, Bull. Chem. Soc. Jpn. 1973, 46, 2490-2492
32. H. Yoshimoto, H. Itatani, J. Catal. 1973, 31, 8-12
33. A. Shiotani, M. Yoshikiyo, H. Itatani, J. Mol. Catal. 1983, 18, 23-31
34. A, Shiotani, H, Itatani, T. Inagaki, J. Mol. Catal. 1986, 34, 57-66.
35. Y. Mohri, Seni Gakkaishi 1994, 50, 96-101
36. J. A. Kreuz, J. R. Edman, Adv. Mater. 1998, 10, 1229.
37. A NineSigma™ proposal request (#11222-1) was issued in Oct. 2008, entitled "Benzene Ring Catalytic Coupling Technology", in which a multi-billion dollar chemical manufacturer targeted the development of novel catalysts for the direct coupling of substituted aromatics.
38. Aerobic oxidation of bixylyl to biphthalate has been accomplished under conditions similar to the well-established industrial processes for benzylic oxidation, such as the Mid-Century process for commercial production of terephthalic acid from p-xylene:, T. Kumano, A. Ogoshi, Japanese Patent 34227, 2003.
39. H. Itatani, A. Shiotani, H. Yoshimoto, M, Yoshikiyo, A. Yokota, Japanese Patent 79324, 1980.
40. See, for example
41. T. Nishimura, T. Onoue, K. Ohe, S. Uemura, Tetrahedron Lett. 1998, 39, 6011-6014
42. S. R. Fix, J. L. Brice, S. S. Stahl, Angew. Chem. 2002, 114, 172-174
43. Angew. Chem. Int. Ed. 2002, 41, 164-166
44. T. Nishimura, H. Araki, Y. Maeda, S. Uemura, Org. Lett. 2003, 5, 2997-2999
45. M. M. S. Andappan, P. Nilsson, M. Larhed, Chem. Commun. 2004, 218-219
46. R. A. Sheldon, I. W. C. E. Arends, G.-J. ten Brink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774-781
47. K. S. Yoo, C. P. Park, C. H. Yoon, S. Sakaguchi, J. O'Neill, K. W. Jung, Org. Lett. 2007, 9, 3933-3935
48. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072-5074.
49. H. C. Brown, D. H. McDaniel, J. Am. Chem. Soc. 1955, 77, 3752-3755.
50. 2 in a 2:1 stoichiometry. See:, B. A. Steinhoff, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 11268-11278.
51. See Supporting Information for the X-ray crystallographic data.
52. [4c] and the following
53. R. S. Shue, J. Am. Chem. Soc. 1971, 93, 7116-7117
54. L. M. Stock, K. Tse, L. J. Vorvich, S. A. Walstrum, J. Org. Chem. 1981, 46, 1757-1759
55. M. Kashima, H. Yoshimoto, H. Itatani, J. Catal. 1973, 29, 92-98
56. L. J. Ackerman, J. P. Sadighi, D. M. Kurtz, J. A. Labinger, J. E. Bercaw, Organometallics 2003, 22, 3884-3890.
57. S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 10848-10849
58. D. L. Davies, S. M. A. Donald, S. A. Macgregor, J. Am. Chem. Soc. 2005, 127, 13754-13755
59. D. Garcia-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066-1067
60. D. Balcells, E. Clot, O. Eisenstein, Chem. Rev. 2010, 110, 749-823.
61. [12] and the following references. In cases where literature data are not available (4-fluoro-, 2,4,6-trifluoro-, 2,3,5-trifluoro- and 2-fluoro-4- trifluoromethylpyridinium), the pKa values are those reported in SciFinder Scholar based on calculations using Advanced Chemistry Development (ACD/Labs) Software V 11.02
62. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463
63. M. R. Chakrabarty, C. S. Handloser, M. W. Mosher, J. Chem. Soc. Perkin Trans. 2 1973, 7, 938-942
64. K. Clarke, K. Rothwell, J. Chem. Soc. 1960, 1885-1895.