Synthesis of diaryl selenides using the in situ reagent SeCl 2

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 665-669

  Zade, Sanjio S ^a   Panda, Snigdha ^a   Singh, Harkesh B ^a   Wolmershäuser, Gotthelf ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

2 Phenyl 1,2 benzisoselenazol 3(2H) one; Benzamide; Diorganoselenide; Lithiation; Selenium dichloride

Indexed keywords

1 BROMO 2 METHYLNAPHTHALENE; 2 TOLYL BROMIDE; 2,6 DIMETHYL 4 TERT BUTYL 1 BROMOBENZENE; BENZAMIDE DERIVATIVE; BROMOBENZENE; REAGENT; SELENIDE; SELENIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; GRIGNARD REACTION; REACTION ANALYSIS;

EID: 11144266599     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.125     Document Type: Article

References (59)

1. C. Paulmier Selenium Reagents and Intermediates in Organic Synthesis 1985 Pergamon Oxford
2. S. Patai Z. Rappoport Chemistry of Organoselenium and Tellurium Compounds 1987 John Wiley & Sons New York
3. T.G. Back Organoselenium Chemistry: A Practical Approach 1999 Oxford University Press Oxford
4. T. Wirth Topics in Current Chemistry Vol. 208 2000 Springer Heidelberg
5. L. Engman, D. Stern, M. Pelcmanl, and C.-M. Andersson J. Org. Chem. 59 1994 1973 1979
6. C.-M. Andersson, A. Hallberg, and T. Hoegberg Adv. Drug Res. 28 1996 65 180
7. J. Malmstrom, M. Jonsson, I.A. Cotgreave, L. Hammarstrom, M. Sjodin, and L. Engman J. Am. Chem. Soc. 123 2001 3434 3440
8. G. Mugesh, and H.B. Singh Chem. Soc. Rev. 29 2000 347 357
9. G. Mugesh, W.-W. du Mont, and H. Sies Chem. Rev. 101 2001 2125 2179
10. H.J. Gysling Coord. Chem. Rev. 42 1982 133 244
11. E.G. Hope, and W. Levason Coord. Chem. Rev. 122 1993 109 170
12. W. Levason, S.D. Orchard, and G. Reid Coord. Chem. Rev. 225 2002 159 199
13. Hiroi, K. In Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.; 2000; Vol. 1, pp 67-79
14. J. Gladysz, J.L. Hornby, and J.E. Garbe J. Org. Chem. 43 1978 1204 1208
15. D.L. Klayman, and T.S. Griffin J. Am. Chem. Soc. 95 1973 197 199
16. C.O. Kienitz, C. Thöne, and P.G. Jones Inorg. Chem. 35 1996 3990 3997
17. A. Krief, and M. Derock Tetrahedron Lett. 43 2002 3083 3086
18. L. Syper, and J. Mlochowski Tetrahedron 44 1988 6119 6130
19. D.P. Thompson, and P. Boudjouk J. Org. Chem. 53 1988 2109 2112
20. D.J. Sandman, J.C. Stark, and B.M. Foxman Organometallics 1 1982 739 742
21. D.J. Sandman, J.C. Stark, L.A. Acampora, and P. Gagne Organometallics 2 1983 549 551
22. C.M. Bates, C.P. Morley, M.B. Hursthouse, and K.M.A. Malik J. Organomet. Chem. 489 1995 C60 C61
23. S.D. Apte, H.B. Singh, and R.J. Butcher J. Chem. Res. (S) 2000 160 161
24. J. Chem. Res. (M) 2000 0559 0569
25. A. Panda, S.C. Menon, H.B. Singh, and R.J. Butcher J. Organomet. Chem. 623 2001 87 94
26. O. Foss Inorg. Synth. 4 1953 88 93
27. A.W. Cordes, S.H. Glarum, R.C. Haddon, R. Hallford, R.G. Hicks, D.K. Kennepohl, R.T. Oakley, T.T.M. Palstra, and S.R. Scott J. Chem. Soc., Chem. Commun. 1992 1265 1266
28. A.W. Cordes, C.D. Bryan, W.M. Davis, R.H.S. de Laat, H. Glarum, J.D. Goddard, R.C. Haddon, R.G. Hicks, and D.K. Kennepohl J. Am. Chem. Soc. 115 1993 7232 7239
29. J. Milne Polyhedron 4 1985 65 68
30. M.R. Bryce, and A. Chesney Chem. Commun. 1995 195 196
31. A. Maaninen, T. Chivers, M. Parvez, J. Pietikäinen, and R.S. Laitinen Inorg. Chem. 1999 4093 4097
32. J. Konu, A. Maaninen, K. Paananen, P. Ingman, R.S. Laitinen, T. Chivers, and J. Valkonen Inorg. Chem. 41 2002 1430 1435
33. T. Maaninen, T. Chivers, R.S. Laitinen, G. Schatte, and M. Nissinen Inorg. Chem. 39 2000 5341 5347
34. T. Maaninen, T. Chivers, R.S. Laitinen, and E. Wegelius Chem. Commun. 2000 759 760
35. 4). Evaporation of the solvent afforded a gray-colored solid, which was purified by passing through a silica gel column (petroleum ether, 60-80) and recrystallized from petroleum ether (60-80) to give colorless crystals of the desired compound
36. 1H NMR data for 3 and 4 match with reported values M. Taniguchi, and T. Onami J. Org. Chem. 69 2004 915 920
37. G. Mugesh, A. Panda, H.B. Singh, N.S. Punekar, and R.J. Butcher J. Am. Chem. Soc. 123 2001 839 850
38. G. Mugesh, A. Panda, S. Kumar, S.D. Apte, H.B. Singh, and R.J. Butcher Organometallics 21 2002 884 892
39. 34Se: C, 71.85; H, 8.53. Found: C, 71.63; H, 9.07
40. 3): δ 355
41. M. Schlosser Tetrahedron 50 1994 5845 6128
42. G. Mugesh, and H.B. Singh Acc. Chem. Res. 35 2002 226 236
43. 2 (2.5 mmol) solution, prepared separately in a three-necked flask, was added to the dilithiated benzamide solution dropwise at -78°C. The resulting solution was then allowed to warm to rt. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was filtered through Celite, and dried over sodium sulfate. Evaporation of the solvent afforded a colorless solid, which was purified by silica gel column chromatography using dichloromethane as eluent
44. R. Weber, and M. Renson Bull. Soc. Chim. Fr. 1976 1124 1126
45. C. Lambert, A. Welter, L.E. Christiaens, and N. Dereu Synth. Commun. 21 1991 85 98
46. Christiaens, L. E.; Wirtz, P. Eur. Pat. Appl. EP 44453, 1982; Chem. Abstr. 1982, 96, 199699v
47. L. Engman, and A. Hallberg J. Org. Chem. 54 1989 2964 2965
48. M.C. Fong, and C.H. Schiesser Tetrahedron Lett. 36 1995 7329 7332
49. M.C. Fong, and C.H. Schiesser J. Org. Chem. 62 1997 3103 3108
50. P.V. Jacquemin, L.E. Christiaens, M.J. Renson, M.J. Evers, and N. Dereu Tetrahedron Lett. 33 1992 3863 3866
51. K. Kloc, J. Mlochowski, M. Osajda, L. Syper, and H. Wojtowicz Tetrahedron Lett. 43 2002 4071 4074
52. R. Lesser, and R. Weiss Ber. Dtsch. Chem. Ges. 57 1924 1077 1082
53. 2Se: C, 64.60; H, 6.66; N, 5.79. Found: C, 64.10; H, 6.38; N, 6.05
54. V.C. Christov, and I.K. Ivanov Heterocycl. Commun. 9 2003 629 634
55. M. Osajda, and J. Mlochowski Synth. Commun. 33 2003 1301 1307
56. K. Kloc, M. Osajda, and J. Mlochowski Chem. Lett. 2001 826 827
57. V.A. Potapov, S.V. Amosova, B.V. Petrov, A.A. Starkova, and R.N. Malyushenko Sulfur Lett. 21 1998 109 114
58. T.G. Back, B.P. Dyck, and S. Nan Tetrahedron 55 1999 3191 3208
59. For a detailed description see supporting information. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-250001. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ]