A convenient synthetic route for alkynylselenides from alkynyl bromides and diaryl diselenides employing copper(I)/imidazole as novel catalyst system

Tetrahedron Letters

Volumn 49, Issue 35, 2008, Pages 5172-5174

  Sharma, Anuj ^a   Schwab, Ricardo S ^b   Braga, Antonio L ^b   Barcellos, Thiago ^b   Paixão, Marcio W ^c  

^a UNIVERSITY OF ARIZONA   (United States)

^b FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL BROMIDE DERIVATIVE; ALKYNYL GROUP; ALKYNYLSELENIDE DERIVATIVE; CHALCOGEN; COPPER; DIARYL DISELENIDE DERIVATIVE; IMIDAZOLE; MAGNESIUM; ORGANOSELENIUM DERIVATIVE; ZINC;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; STOICHIOMETRY; SYNTHESIS;

EID: 47049091856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.071     Document Type: Article

References (47)

1. See for example the following:. Nicolaou K.C., and Petasis N.A. Selenium in Natural Products Synthesis (1984), CIS, Pennsylvania
2. Patai, S.; Rappoport, Z.; Wiley, C. In The Chemistry of Organic Selenium and Tellurium ompounds, 1987; Vol. 2.
3. Back T.G. Organoselenium Chemistry: A Practical Approach (1999), Oxford University Press, New York
4. Liu G., Huth J.R., Olejniczak E.T., Mendoza R., DeVries P., Leitza S., Reilly E.B., Okasinski G.F., Fesik S.W., and von Geldern T.W. J. Med. Chem. 44 (2001) 1202
5. Mugesh G., du Mont W.-W., and Sies H. Chem. Rev. 101 (2001) 2125
6. Krief A., and Derock M. Tetrahedron Lett. 43 (2002) 3083
7. Szczepina M.G., Johnston B.D., Yuan Y., Svensson B., and Pinto B.M. J. Am. Chem. Soc. 126 (2004) 12458
8. Braga A.L., Lüdtke D.S., Paixão M.W., Alberto E.E., Stefani H.A., and Juliano L. Eur. J. Org. Chem. (2005) 4260-4264
9. Okamoto Y. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Organic Selenium and Tellurium Compounds Vol. 1 (1986), Wiley, Chichester, U.K. Chapter 10
10. Hellberg J., Remonen T., Johansson M., Inganäs O., Theander M., Engman L., and Eriksson P. Synth. Met. 84 (1997) 251
11. Ando T., Kwon T.S., Kitagawa A., Tanemura T., Kondo S., Kunisada H., and Yuki Y. Macromol. Chem. Phys. 197 (1996) 2803
12. Takagi K., Nishikawa Y., Kwon T.S., Kunisada H., and Yuki Y. Polym. J. 32 (2000) 970
13. Stuhr-Hansen N., Beckers E.H.A., Engman L., and Janssen R.A. J. Heterocycl. Chem. 16 (2005) 656
14. Magriotis P.A., Brown J.T., and Scott M.E. Tetrahedron Lett. 32 (1991) 5047
15. Comasseto J.V. J. Organomet. Chem. 253 (1983) 131
16. Braga A.L., Reckziegel A., Silveira C.C., and Comasseto J.V. Synth. Commun. 24 (1994) 1165
17. Kataoka T., Watanabe S., and Yamamoto K. Tetrahedron Lett. 40 (1999) 931
18. Braga A.L., Comasseto J.V., and Petragnani N. Synthesis (1984) 240
19. Ma Y., and Qian C. Tetrahedron Lett. 41 (2000) 945
20. Petrov M., Radchenko S.I., Kupin V.S., and Petrov A.A. J. Org. Chem. (USSR) 9 (1973) 683
21. Comasseto J.V., Menezes P.H., Stefani H.A., Zeni G., and Braga A.L. Tetrahedron 52 (1996) 9687
22. Tingolli M., Tiecco M., Testaferri L., and Temperini A. Tetrahedron 51 (1995) 4691
23. Magriotis P.A., Brown J.T., and Scott M.E. Tetrahedron Lett. 32 (1991) 5047
24. Huang X., and Ma Y. Synthesis (1997) 312
25. Zhu L.S., Huang Z.Z., and Huang X.J. J. Chem. Res. (S) (1996) 112
26. Yang D.Y., and Huang X.J. J. Organomet. Chem. 543 (1997) 165
27. Tiecco M., Testaferri L., Temperini A., Bagnoli L., Marini F., Santi C., and Terlizzi R. Eur. J. Org. Chem. (2004) 3447
28. Das J.P., Roy U.K., and Roy S. Organometallics 24 (2005) 6136
29. Kundu A., and Roy S. Organometallics 19 (2000) 105
30. Braga A.L., Reckziegel A., Menezes P.H., and Stefani H.A. Tetrahedron Lett. 34 (1993) 393
31. Braga A.L., Silveira C.C., Reckziegel A., and Menezes P.H. Tetrahedron Lett. 34 (1993) 8041
32. Tingoli M., Tiecco M., Testaferri L., and Balducci R. Synlett (1993) 211
33. For Glaser reaction:. Youngblood W.J., Gryko D.T., Lammi R.K., Bocian D.F., Holten D., and Lindsey J.S. J. Org. Chem. 67 (2002) 2111
34. For Ullmann reaction:. Hassan J., Sevignn M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
35. Aromatic Finkelstein reaction:. Klapers A., and Buchwald S.L.J. Am. Chem. Soc. 124 (2002) 14844
36. Amination reaction:. Ma D., Cai Q., and Zhang H. Org. Lett. 5 (2003) 2453
37. N-Arylation:. Klapers A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421
38. Miscellaneous:. Fouquet G., and Schlosser M. Angew Chem., Int. Ed. 13 (1974) 82
39. Chan T.R., Hilgraf R., Sharpless K.B., and Fokin V.V. Org. Lett. 6 (2004) 2853
40. Paixão M.W., Weber M., Braga A.L., de Azeredo J.B., Deobald A.M., and Stefani H. Tetrahedron Lett. 49 (2008) 2366
41. Bieber L.W., da Silva M.F., and Menezes P.H. Tetrahedron Lett. 45 (2004) 2735-2737
42. Schareina T., Zapf A., Magerlein W., Muller N., and Beller M. Synlett (2007) 555
43. Schareina T., Zapf A., Magerlein W., Muller N., and Beller M. Chem. Eur. J. 13 (2007) 6249
44. 13C NMR spectroscopic data and mass analysis.
45. Taniguchi N., and Onami T. J. Org. Chem. 69 (2004) 915
46. Taniguchi N., and Onami T. Synlett 829 (2003)
47. Kumar S., and Engman L. J. Org. Chem. 71 (2006) 5400