Iron-mediated direct suzuki-miyaura reaction: A new method for the ortho -arylation of pyrrole and pyridine

Organic Letters

Volumn 12, Issue 12, 2010, Pages 2694-2697

  Wen, Jun ^a,b   Qin, Song ^a,b   Ma, Li Fang ^a,b   Dong, Liang ^a,b   Zhang, Ji ^a,b   Liu, Shan Shan ^a,b   Duan, Yi Shu ^a,b   Chen, Shan Yong ^a,b   Hu, Chang Wei ^a,b   Yu, Xiao Qi ^a,b  

^a China   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; IRON; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS; IRON; MOLECULAR STRUCTURE; PYRIDINES; PYRROLES; STEREOISOMERISM;

EID: 77953575860     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100838m     Document Type: Article

References (66)

1. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513
2. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
3. Miyaura, N. Top. Curr. Chem. 2002, 219, 11
4. Torssell, K. G. B. Natural Product Chemistry; Wiley: Chichester, 1983.
5. Thomson, R. H. The Chemistry of Natural Products; Blackie: Glasgow, 1985.
6. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359
7. Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651
8. Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, 2005.
9. Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818
10. Tang, Z. Y.; Hu, Q. S. J. Am. Chem. Soc. 2004, 126, 3058
11. Steinhuebel, D.; Baxter, J. M.; Palucki, M.; Davies, I. W. J. Org. Chem. 2005, 70, 10124
12. So, C. M.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 8059
13. Kakiuchi, F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936
14. Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220
15. Giri, R.; Maugel, N.; Li, J.; Wang, D.; Breazzano, S. P.; Saunders, L. B.; Yu, J. J. Am. Chem. Soc. 2007, 129, 3510
16. Shi, Z.; Li, B.; Wan, X.; Chen, J.; Fang, Z.; Cao, B.; Qing, C.; Wang, Y. Angew. Chem., Int. Ed. 2007, 46, 5554
17. Yang, S.; Sun, C.; Fang, Z.; Li, B.; Li, Y.; Shi, Z. Angew. Chem., Int. Ed. 2008, 47, 1473
18. General reviews
19. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217
20. Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624
21. Iron Catalysis in Organic Chemistry: Reactions and Applications; Plietker, B., Ed.; Wiley-VCH: Weinheim, 2008.
22. Correa, A.; Mancheno, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108
23. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500
24. Sarhan, A. A. O.; Bolm, C. Chem. Soc. Rev. 2009, 38, 2730
25. Fürstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856
26. Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686
27. Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J. Org. Lett. 2005, 7, 1219
28. Sapountzis, I.; Lin, W.; Kofink, C. C.; Despotopoulou, C.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 1654
29. Bica, K.; Gaertner, P. Org. Lett. 2006, 8, 733
30. Ottesen, L. K.; Ek, F.; Olsson, R. Org. Lett. 2006, 8, 1771
31. Kischel, J.; Mertins, K.; Michalik, D.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2007, 349, 865
32. Guérinot, A.; Reymond, S.; Cossy, J. Angew. Chem., Int. Ed. 2007, 46, 6521
33. Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844
34. Cahiez, G.; Habiak, V.; Gager, O. Org. Lett. 2008, 10, 2389
35. Carril, M.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 4862
36. Marquand, P. L.; Tsui, G. C.; Whitney, J. C. C.; Tam, W. J. Org. Chem. 2008, 73, 7829
37. Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2008, 73, 9061
38. Czaplik, W. M.; Mayer, M.; Wangelin, A. J. Angew. Chem., Int. Ed. 2009, 48, 607
39. Loska, R.; Volla, C. M. R.; Vogel, P. Adv. Synth. Catal. 2008, 350, 2859
40. Zou, T.; Pi, S.-S.; Li, J.-H. Org. Lett. 2009, 11, 453
41. Fujiwara, M.; Kawatsura, M.; Hayase, S.; Nanjo, M.; Itoh, T. Adv. Synth. Catal. 2009, 351, 123
42. Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 6505
43. Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858
44. Li, Z.; Yu, R.; Li, H. Angew. Chem., Int. Ed. 2008, 47, 7497
45. Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925
46. Moreau, B.; Wu, J. Y.; Ritter, T. Org. Lett. 2009, 11, 337
47. Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817
48. Vallée, F.; Mousseau, J. J.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 1514
49. Wen, J.; Zhang, J.; Chen, S.-Y.; Li, J.; Yu, X.-Q. Angew. Chem., Int. Ed. 2008, 47, 8897
50. Thompson, A. E.; Hughes, G.; Batsanov, A. S.; Bryce, M. R.; Parry, P. R.; Tarbit, B. J. Org. Chem. 2005, 70, 388
51. Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282
52. Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 3484
53. Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586
54. Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Baidossi, M.; Ponde, D. E.; Sasson, Y. J. Chem. Soc., Perkin Trans. 2000, 2, 1809
55. Godula, K.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2005, 127, 3648
56. Yanagisawa, S.; Ueda, K.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 4673
57. Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926
58. Li, M.; Hua, R. Tetrahedron Lett. 2009, 50, 1478
59. Du Bois, J.; Mizoguchi, T. J.; Lippard, S. J. Coord. Chem. Rev 2000, 200-202, 443
60. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L. Chem. Rev. 2004, 104, 939
61. MacBeth, C. E.; Golombek, A. P.; Young, V. G., Jr.; Yang, C.; Kuczera, K.; Hendrich, M. P.; Borovik, A. S. Science 2000, 289, 938
62. Miyaura, N. J. Organomet. Chem. 2002, 653, 54
63. Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005, 127, 9298
64. Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Lledós, A.; Maseras, F. J. Organomet. Chem. 2006, 691, 4459
65. See Supporting Information for details.
66. Ghosh, A.; Oliveira, F. T. d.; Yano, T.; Nishioka, T.; Beach, E. S.; Kinoshita, I.; MuÈnck, E.; Ryabov, A. D.; Horwitz, C. P.; Collins, T. J. J. Am. Chem. Soc. 2005, 127, 2505