Oxidative nickel-air catalysis in C-H arylation: Direct cross-coupling of Azoles with arylboronic acids using air as sole oxidant

ChemCatChem

Volumn 2, Issue 11, 2010, Pages 1403-1406

  Hachiya, Hitoshi ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Arylation; Boron; Heterocycles; Nickel; Oxidation

Indexed keywords

EID: 79551686845     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201000223     Document Type: Article

References (100)

1. Modern Organonickel Chemistry (Ed: Y. Tamaru), Wiley-VCH, Weinheim, 2006;
2. Recent Advances in Organonickel Chemistry (Ed: T. Jamison), Tetrahedron 2006, 62, 7493-7610.
3. K. Muñiz, J. Streuff, C. H. Hövelmann, A. Núñez, Angew. Chem. 2007, 119, 7255; Angew. Chem. Int. Ed. 2007, 46, 7125;
4. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Angew. Chem. 2010, 122, 2248; Angew. Chem. Int. Ed. 2010, 49, 2202; see also
5. J. M. Grill, J. W. Ogle, S. A. Miller, J. Org. Chem. 2006, 71, 9291.
6. Limited successful examples:
7. W. Yin, C. He, M. Chen, H. Zhang, A. Lei, Org. Lett. 2009, 11, 709;
8. T. Truong, J. Alvarado, L. D. Tran, O. Daugulis, Org. Lett. 2010, 12, 1200;
9. N. Matsuyama, M. Kitahara, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2358.
10. Reviews:
11. S. S. Stahl, Angew. Chem. 2004, 116, 3480; Angew. Chem. Int. Ed. 2004, 43, 3400;
12. M. S. Sigman, M. J. Schultz, Org. Biomol. Chem. 2004, 2, 2551;
13. T. Nishimura, S. Uemura, Synlett 2004, 201;
14. B. M. Stoltz, Chem. Lett. 2004, 33, 362;
15. K. M. Gligorich, M. S. Sigman, Chem. Commun. 2009, 3854.
16. G. Wilke, H. Schott, P. Heimbach, Angew. Chem. 1967, 79, 62; Angew. Chem. Int. Ed. Engl. 1967, 6, 92;
17. S. Otsuka, A. Nakamura, Y. Tatsuno, J. Am. Chem. Soc. 1969, 91, 6994;
18. S. Yao, E. Bill, C. Milsmann, K. Wieghardt, M. Driess, Angew. Chem. 2008, 120, 7218; Angew. Chem. Int. Ed. 2008, 47, 7110.
19. Recent reviews:
20. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
21. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200;
22. L. C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35;
23. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173;
24. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222;
25. L. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013;
26. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013;
27. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074;
28. A. A. Kulkarni, O. Daudulis, Synthesis 2009, 4087;
29. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196; Angew. Chem. Int. Ed. 2009, 48, 5094;
30. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976; Angew. Chem. Int. Ed. 2009, 48, 9792;
31. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677;
32. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147;
33. A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2010, 122, 2140; Angew. Chem. Int. Ed. 2010, 49, 2096.
34. Selected examples:
35. F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698;
36. F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, S. Murai, J. Am. Chem. Soc. 2004, 126, 2706;
37. F. Kakiuchi, Y. Matsuura, S. Kan, N. Chatani, J. Am. Chem. Soc. 2005, 127, 5936;
38. X. Chen, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 12634;
39. R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510;
40. Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, Y. Wang, Angew. Chem. 2007, 119, 5650; Angew. Chem. Int. Ed. 2007, 46, 5554;
41. T. Vogler, A. Studer, Org. Lett. 2008, 10, 129;
42. B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949;
43. S. Kirchberg, T. Vogler, A. Studer, Synlett 2008, 2841;
44. I. Ban, T. Sudo, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 3607;
45. H. Ge, M. J. Niphakis, G. J. Georg, J. Am. Chem. Soc. 2008, 130, 3708;
46. D.-H. Wang, M. Wasa, R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 7190;
47. B.-F. Shi, N. Maugel, Y.-H. Zhang, J.-Q. Yu, Angew. Chem. 2008, 120, 4960; Angew. Chem. Int. Ed. 2008, 47, 4882;
48. J. Wen, J. Zhang, S.-Y. Chen, J. Li, X.-Q. Yu, Angew. Chem. 2008, 120, 9029; Angew. Chem. Int. Ed. 2008, 47, 8897;
49. S. Miyamura, H. Tsurugi, T. Satoh, M. Miura, J. Organomet. Chem. 2008, 693, 2438;
50. H. Zhou, W.-J. Chung, Y.-H. Xu, T.-P. Loh, Chem. Commun. 2009, 3472;
51. S. Kirchberg, R. Fröhlich, A. Studer, Angew. Chem. 2009, 121, 4299; Angew. Chem. Int. Ed. 2009, 48, 4235;
52. T. Nishikata, A. R. Abela, S. Huang, B. H. Lipshutz, J. Am. Chem. Soc. 2010, 132, 4978.
53. Direct C-C bond formation from C-H bond with other organometallic reagents; Sn:
54. S. Oi, S. Fukita, Y. Inoue, Chem. Commun. 1998, 2349;
55. X. Chen, J.-J. Li, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 78;
56. H. Kawai, Y. Kobayashi, S. Oi, Y. Inoue, Chem. Commun. 2008, 1464; Zn:
57. J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 5858;
58. N. Yoshikai, A. Matsumoto, J. Norinder, E. Nakamura, Angew. Chem. 2009, 121, 2969; Angew. Chem. Int. Ed. 2009, 48, 2925;
59. M. Tobisu, I. Hyodo, N. Chatani, J. Am. Chem. Soc. 2009, 131, 12070; Si:
60. S. Yang, B. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 6066;
61. H. Zhou, Y.-H. Xu, W.-J. Chung, T.-P. Loh, Angew. Chem. 2009, 121, 5459; Angew. Chem. Int. Ed. 2009, 48, 5355; and ref.[2b].
62. D.-H. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 17676;
63. S. Yang, C. Sun, Z. Fang, B. Li, Y. Li, Z. Shi, Angew. Chem. 2008, 120, 1495; Angew. Chem. Int. Ed. 2008, 47, 1473;
64. 2 catalysis with arylzincs:
65. 2 as the sole oxidant:
66. T. Yokota, M. Tani, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2003, 125, 1476;
67. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072;
68. D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315.
69. Only one precedent for the oxidative direct arylation of electron-deficient arenes under palladium catalysis: Y. Wei, J. Kan, M. Wang, W. Su, M. Hong, Org. Lett. 2009, 11, 3346.
70. Recent advances in nickel-catalyzed direct coupling of heteroarenes with organic halides or pseudohalides:
71. J. Canivet, J. Yamaguchi, I. Ban, K. Itami, Org. Lett. 2009, 11, 1733;
72. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 1737;
73. O. Kobayashi, D. Uraguchi, T. Yamakawa, Org. Lett. 2009, 11, 2679;
74. N. Matsuyama, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 4156.
75. 2, the reaction did not proceed at all, even in the presence of NaOtBu; S. Yanagisawa, K. Ueda, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 4673.
76. Even with the modified system, benzothiazole coupled sluggishly with 4-methylphenylboronic acid (2a) to furnish the arylated product in only 19% GC yield. The reactions with other heteroarenes such as benzimidazole and benzothiophene were unsuccessful.
77. T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390;
78. J. M. Murphy, X. Liao, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 15434. In general, the pinacolboronic esters showed lower reactivity to the parent boronic acids. For example, benzoxazole (1a) sluggishly coupled with 4-biphenylyl pinacolboronic ester under the standard conditions (ca.15% GC yield vs 3ad in Table2). However, in the case of the electron-deficient aryl groups, the activity of pinacol esters was comparable.
79. E. Wenschuh, R. Zimmering, Z. Chem. 1987, 27, 448;
80. W. J. Marshall, V. V. Grushin, Can. J. Chem. 2005, 83, 640.
81. In the absence of phen, a somewhat lower yield (15%) of 5af was detected.
82. Base-assisted cupration of heteroarenes:
83. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404;
84. L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett. 2008, 10, 3081;
85. F. Besselièvre, S. Piguel, F. Mahuteau-Betzer, D. S. Grierson, Org. Lett. 2008, 10, 4029;
86. T. Yoshizumi, H. Tsurugi, T. Satoh, M. Miura, Tetrahedron Lett. 2008, 49, 1598;
87. S. Yotphan, R. G. Bergman, J. A. Ellman, Org. Lett. 2009, 11, 1511;
88. T. Yoshizumi, T. Satoh, K. Hirano, D. Matsuo, A. Orita, J. Otera, M. Miura, Tetrahedron Lett. 2009, 50, 3273;
89. D. Zhao, W. Wang, F. Yang, J. Lan, L. Yang, G. Gao, J. You, Angew. Chem. 2009, 121, 3346; Angew. Chem. Int. Ed. 2009, 48, 3296;
90. T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 3072;
91. F. Besselièvre, S. Piguel, Angew. Chem. 2009, 121, 9717; Angew. Chem. Int. Ed. 2009, 48, 9553;
92. T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900.
93. Indeed, in some cases, a detectable amount of phenol arising from arylboronic acid was detected by GC-MS, indicating the insitu formation of peroxide; palladium analogues:
94. C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829;
95. S. Wacharasindhu, S. Bardhan, Z.-K. Wan, K. Tabei, T. S. Mansour, J. Am. Chem. Soc. 2009, 131, 4174.
96. U. Mitschke, P. Bäuerle, J. Mater. Chem. 2000, 10, 1471;
97. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
98. D. Leung, W. Du, C. Hardouin, H. Cheng, I. Hwang, B. F. Cravatt, D. L. Boger, Bioorg. Med. Chem. Lett. 2005, 15, 1423;
99. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651;
100. G. S. He, L.-S. Tan, Q. Zheng, P. N. Prasad, Chem. Rev. 2008, 108, 1245.