A simple copper salt-catalyzed synthesis of unsymmetrical diaryl selenides and tellurides from arylboronic acids with diphenyl diselenide and ditelluride

Synlett

Volumn , Issue 13, 2005, Pages 2007-2010

  Wang, Lei ^a,b   Wang, Min ^a   Huang, Fuping ^a  

^a HUAIBEI NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Arylboronic acids; Copper salt; Diaryl selenides; Diaryl tellurides; Diphenyl diselenide; Diphenyl ditelluride

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER DERIVATIVE; DIMETHYL SULFOXIDE; SELENIDE; SODIUM CHLORIDE; TELLURIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; PHASE TRANSITION; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 23944469122     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871936     Document Type: Article

References (57)

1. (a) The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1986.
2. (b) The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 2; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1987.
3. (c) Krief, A. In Comprehensive Organometallic Chemistry; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 85-192.
4. (d) Krief, A. In Comprehensive Organometallic Chemistry II, Vol. 11; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: New York, 1995, Chap. 13.
5. (e) Organoselenium Chemistry: A Practical Approach; Back, T. G., Ed.; Oxford University Press: New York, 1999.
6. (f) Ip, C. J. Nutr. 1998, 128, 1845.
7. (g) Ip, C.; Lisk, D. J.; Ganther, H.; Thompson, H. J. Anticancer Res. 1997, 17, 3195.
8. (h) Organoselenium Chemistry, In Topics in Current Chemistry, Vol. 208; Wirth, T., Ed.; Springer-Verlag: Heidelberg, 2000.
9. (a) Ranu, B. C.; Mandal, T. J. Org. Chem. 2004, 69, 5793.
10. (b) Ranu, B. C.; Mandal, T.; Samanta, S. Org. Lett. 2003, 5, 1439.
11. (c) Bao, W.; Zheng, Y.; Zhang, Y.; Zhou, J. Tetrahedron Lett. 1996, 37, 9333.
12. (d) Bao, W.; Zhang, Y. Synlett 1996, 1187.
13. (e) Fukuzawa, S.; Niimoto, Y.; Fujinami, T.; Sakai, S. Heteroat. Chem. 1990, 1, 491.
14. (f) Sakakibara, M.; Katsumata, K.; Watanabe, Y.; Toru, T.; Ueno, Y. Synthesis 1992, 377.
15. (g) Detty, M. R. J. Org. Chem. 1980, 45, 274.
16. (h) Wang, L.; Zhang, Y. Heteroat. Chem. 1999, 10, 203.
17. (i) Nishino, T.; Okada, M.; Kuroki, T.; Watanabe, T.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67, 8696.
18. (j) Bieber, L. W.; Sa, A. C. P. F.; Menezes, P. H.; Goncalves, S. M. C. Tetrahedron Lett. 2001, 42, 4597.
19. (a) Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Christol, H. Organometallics 1985, 4, 657.
20. (b) Zhang, Y.; Guo, H. Heteroat. Chem. 2001, 12, 539.
21. (c) Vasil'ev, A. A.; Engman, L.; Storm, J. P.; Andersson, C.-M. Organometallics 1999, 18, 1318.
22. (d) Gujadhur, R. K.; Venkataraman, D. Tetrahedron Lett. 2003, 44, 81.
23. (e) Osuka, A.; Ohmasa, N.; Suzuki, H. Synthesis 1982, 857.
24. (f) In the absence of any additive, the reaction of with iodobenzene in liquid ammonia only get 3% yield of diphenylselenide. See: Penenory, A. B.; Pierini, A. B.; Rossi, R. A. J. Org. Chem. 1984, 49, 3834.
25. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
26. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
27. (a) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2003, 44, 4927.
28. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
29. Chan, D. M. T.; Monaco, K. L.; Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
30. (a) Tsukamoto, H.; Sato, M.; Kondo, Y. Chem. Commun. 2004, 1200.
31. (b) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893.
32. (a) Lan, J. B.; Chen, L.; Yu, X. Q.; You, J. S.; Xie, R. G. Chem. Commun. 2004, 188.
33. (b) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892.
34. (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
35. Zou, G.; Zhu, J.; Tang, J. Tetrahedron Lett. 2003, 44, 8709.
36. Patel, S. J.; Jamison, T. F. Angew. Chem. Int. Ed. 2003, 42, 1364.
37. Yoshida, M.; Gotou, T.; Ihara, M. Chem. Commun. 2004, 1124.
38. (a) Tang, Z. Y.; Hu, Q. S. J. Am. Chem. Soc. 2004, 126, 3058.
39. (b) Bandgar, B. P.; Bettigeri, S. V.; Phopase, J. Org. Lett. 2004, 6, 2105.
40. (a) Principles and Applications of Organotransition Metal Chemistry; Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G., Eds.; University Science: Mill Valley CA, 1987.
41. (b) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
42. (a) Taniguchi, N.; Onami, T. Synlett 2003, 829.
43. (b) Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
44. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
45. (b) Wasserschield, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39, 3772.
46. (c) DuPont, J.; De Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
47. Kabalka, G. W.; Venkataiah, B. Tetrahedron Lett. 2002, 43, 3703.
48. (a) Molander, G. A.; Ribagorda, M. J. Am. Chem. Soc. 2003, 125, 11148.
49. (b) Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
50. (c) Darses, S.; Michaud, G.; Genêt, J. P. Tetrahedron Lett. 1998, 39, 5045.
51. (d) Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107.
52. (e) Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302.
53. (f) Batey, R. A.; Thadani, A. N. Org. Lett. 1999, 1, 1683.
54. (g) Thadani, A. N.; Batey, R. A. Org. Lett. 2002, 4, 3827.
55. (h) Kabalka, G. W.; Dong, G.; Venkataiah, B. Tetrahedron Lett. 2004, 45, 5139.
56. (i) Kabalka, G. W.; Venkataiah, B.; Dong, G. Org. Lett. 2003, 5, 3803.
57. (j) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649.