Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?

Russian Chemical Bulletin

Volumn 55, Issue 1, 2006, Pages 118-122

  Burukin, A S ^a   Vasil'ev, A A ^a   Merkulova, N L ^b   Struchkova, M I ^a   Zlotin, S G ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b ChemBridge Corporation   (Russian Federation)

Author keywords

1,3 bis(tetrazol 1 yl)benzene; Biaryls; Cross coupling; Phenylboronic acid; Polychloroarenes; Tetrazoles; The Suzuki reaction

Indexed keywords

EID: 33745043082     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-006-0224-0     Document Type: Article

References (56)

1. (a) N. Miyaura and A. Suzuki. Chem. Rev., 1995, 95, 2457;
2. (b) A. Suzuki, in Metal-Catalyzed Cross-Coupling Reactions, Eds F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, Germany, 1998, p. 49;
3. (c) S. Kotha, K. Lahiri, and D. Kashinath, Tetrahedron, 2002, 58, 9633.
4. (a) J. P. Wolfe, R. A. Singer, B. H. Yang, and S. L. Buchwald, J. Am. Chem. Soc., 1999, 121, 9550;
5. (b) A. F. Littke, C. Dai, and G. C. Fu, J. Am. Chem. Soc., 2000, 122, 4020;
6. (c) N. Kataoka, Q. Shelby, J. P. Stambuli, and J. F. Hartwig, J. Org. Chem., 2002, 67, 5553;
7. (d) A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dhigerdissen, and M. Beller, Chem. Commun., 2004, 38;
8. (e) T. E. Barder and S. L. Buchwald, Org. Lett., 2004, 6, 2649;
9. (f) T. J. Colacot and H. A. Shea, Org. Lett., 2004, 6, 3731;
10. (e) B. Liu, K. K. Moffett, R. W. Joseph, and B. D. Dorsey, Tetrahedron Lett., 2005, 46, 1779;
11. (f) A. Tewari, M. Hein, A. Zapf, and M. Beller, Tetrahedron, 2005, 61, 9705.
12. (a) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, and W. A. Herrmann, Angew. Chem., Int. Ed., 2002, 41, 1363;
13. (b) O. Navarro, H. Kaur, P. Mahjoor, and S. P. Nolan, J. Org. Chem., 2004, 69, 3173;
14. (c) H. Lebel, M. K. Janes, A. B. Charette, and S. P. Nolan, J. Am. Chem. Soc., 2004, 126, 5046;
15. (d) K. Arentsen, S. Caddick, F. G. N. Clocke, A. P. Herring, and P. B. Hitchcock, Tetrahedron Lett., 2004, 45, 3511;
16. (e) A.-E. Wang, J. Zhong, J.-H. Xie, K. Li, and Q.-L. Zhou, Adv. Synth. Catal., 2004, 346, 595;
17. (f) C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, and M. B. Andrus, Tetrahedron, 2005, 61, 7438;
18. (g) K. Arensten, S. Caddick, and F. G. N. Clocke, Tetrahedron, 2005, 61, 9710;
19. (h) O. Navarro, N. Marion, N. M. Scott, J. Gonzalez, D. Amoroso, A. Bell, and S. P. Nolan, Tetrahedron, 2005, 61, 9716;
20. (i) W. Huang, J. Quo, Y. Xiao, M. Zhu, G. Zou, and J. Tang, Tetrahedron, 2005, 61, 9783.
21. (a) B. Tao and D. W. Boykin, Tetrahedron Lett., 2002, 43, 4955;
22. (b) L. Ackermann and R. Born, Angew. Chem., Int. Ed., 2005, 44, 2444;
23. (c) G. Miao, P. Yu, and C. M. Baldino, J. Org. Chem., 2005, 70, 2332;
24. (d) J.-H. Li, W.-J. Liu, and Y.-X. Xie, J. Org. Chem., 2005, 70, 5409;
25. (e) A. Corma, H. Garcia, and A. Leyva, Tetrahedron, 2005, 61, 9848.
26. A. K. Gupta, C. Y. Rim, and C. H. Oh, Synlett., 2004, 2227.
27. (a) N. A. Bumagin, V. V. Bykov, and I. P. Beletskaya, Dokl. Akad. Nauk SSSR, 1990, 315, 1133
28. [Dokl. Chem., 1990, 315, 354 (Engl. Transl.)];
29. (b) V. V. Bykov, N. A. Bumagin, and I. P. Beletskaya, Dokl. Akad. Nauk, 1995, 340, 775
30. [Dokl. Chem., 1995 (Engl. Transl.)];
31. (c) N. A. Bumagin and V. V. Bykov, Tetrahedron, 1997, 53, 14437;
32. (d) N. A. Bumagin and V. V. Bykov, Zh. Obshch. Khim., 1996, 66, 1981
33. [J. Gen. Chem., 1996, 66, 1925 (Engl. Transl.)].
34. (a) D. Zim, A. L. Monteiro, and J. Dupont, Tetrahedron Lett., 2000, 41, 8199;
35. (b) E. M. Campi, W. R. Jackson, S. M. Marcuccio, and C. G. M. Naeslund, Chem. Commun., 1994, 2395;
36. (c) C. R. LeBlond, A. T. Andrews, Y. Sun, and J. R. Sowa, Org. Lett., 2001, 3, 1555;
37. (d) D. Ma and Q. Wu, Tetrahedron Lett., 2001, 42, 5279.
38. H. Sajiki, A. Kume, K. Hattori, and K. Hirota, Tetrahedron Lett., 2002, 43, 7247.
39. K. Inada and N. Miyaura, Tetrahedron, 2000, 56, 8657.
40. (a) R. Frenette and R. W. Friesen, Tetrahedron Lett., 1994, 35, 9177;
41. (b) S. Chamoin, S. Houldsworth, and V. Snieckus, Tetrahedron Lett., 1998, 39, 4175;
42. (c) S. Schneider and W. Bannwarth, Angew. Chem., Int. Ed., 2000, 39, 4142.
43. (a) T. Osswald, S. Schneider, S. Wang, and W. Bannwarth, Tetrahedron Lett., 2001, 42, 2965;
44. (b) M. Feuerstein, F. Berthiol, H. Doucet, and M. Santelli, Synlett., 2002, 1807;
45. (c) T. Mino, Y. Shirae, M. Sakamoto, and T. Fujita, Synlett., 2003, 882;
46. (d) I. J. S. Fairlamb, A. R. Kapdi, J. M. Lynam, R. J. K. Taylor, and A. C. Whitwood, Tetrahedron, 2004, 60, 5711;
47. (e) W. Shen, Tetrahedron Lett., 1997, 38, 5575;
48. (d) S. Saito, S. Oh-tani, and N. Miyaura, J. Org. Chem., 1997, 62, 8024;
49. (e) M. Nishimura, M. Ueda, and N. Miyaura, Tetrahedron, 2002, 58, 5779.
50. A. S. Burukin, A. A. Vasil'ev, M. I. Struchkova, V. V. Kachala, and S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim., 2005, 941
51. [Russ. Chem. Bull., Int. Ed., 2002, 54, 964].
52. P. N. Gaponik, V. P. Karavai, I. E. Davshko, M. M. Degtyarik, and A. N. Bogatikov, Khim. Geterotsikl. Soedin., 1990, 1528
53. [Chem. Heterocycl. Compd., 1990, 26, 1274 (Engl.Transl.)].
54. R. Huisgen, C. Axen, and H. Seidl, Chem. Ber., 1965, 98, 2966.
55. A. S. Burukin, A. A. Vasil'ev, A. O. Chizhov, and S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim., 2005, 947
56. [Russ. Chem. Bull., Int. Ed., 2005, 54, 970].