Facile generation of vicinal bromoazides from olefins using TMSN3 and TsNBr2 without any catalyst

Tetrahedron Letters

Volumn 50, Issue 36, 2009, Pages 5083-5087

  Saikia, Indranirekha ^a   Phukan, Prodeep ^a  

^a GAUHATI UNIVERSITY   (India)

Author keywords

, Unsaturated carbonyl compounds; Acrylates; Bromoazidation; Bromoazide; N,N Dibromo p toluenesulfonamide (TsNBr2); Olefin; Styrene; Trimethylsilyl azide (TMSN3)

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; AZIDE; BROMINE DERIVATIVE; CHALCONE DERIVATIVE; CINNAMIC ACID DERIVATIVE; N,N DIBROMO 4 TOLUENESULFONAMIDE; STYRENE DERIVATIVE; TRIMETHYLSILYL AZIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 67650446429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.059     Document Type: Article

References (45)

1. Sheradsky T. In: Patai S. (Ed). The Chemistry of the Azido Group (1971), Interscience, New York 331
2. Scriven E.F.V., and Turnbull K. Chem. Rev. 88 (1988) 297-368
3. Bräse S., Gil C., Knepper K., and Zimmermann V. Angew. Chem., Int. Ed. 44 (2005) 188-5240
4. Boyer J.H. J. Am. Chem.Soc. 73 (1951) 5865
5. Wasserman H.H., Brunner R.K., Buynak J.D., Carter C.G., Oku T., and Robinson R.P. J. Am. Chem. Soc. (1985) 519-521
6. Huisgen R. Angew. Chem., Int. Ed. 2 (1963) 565-598
7. Tornøe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
8. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
9. Amantini D., Fringuelli F., Piermatti O., Pizzo F., Zunino E., and Vaccaro L. J. Org. Chem. 70 (2005) 6526
10. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
11. Kolb H.C., and Sharpless K.B. Drug Discovery Today 8 (2003) 1128-1137
12. Breinbauer R., and Köhn M. ChemBioChem. 4 (2003) 1147-1149
13. Bock V.D., Hiemstra H., and van Maarseveen J.H. Eur. J. Org. Chem. (2006) 51-68
14. Hassner A., and Fowler F.W. J. Org. Chem. 33 (1968) 2686-2691
15. Wasserman H.H., Brunner R.K., Buynak J.D., Carter C.G., Oku T., and Robinson R.P. J. Am. Chem. Soc. 107 (1985) 519-521
16. Van Ende D., and Krief A. Angew. Chem. (1974) 279-280
17. Denis J.N., and Krief A. Tetrahedron 35 (1979) 2901-2903
18. Ranganathan S., Ranganathan D., and Mehrotra A.K. Tetrahedron Lett. 14 (1973) 2265-2268
19. Moorthy S.N., and Devaprabhakara D. Tetrahedron Lett. 16 (1975) 257-260
20. Hantzsch A., and Schümann M. Ber. Dtsch. Chem. Ges. 33 (1900) 522
21. Hassner A., and Levy L.A. J. Am. Chem. Soc. 87 (1965) 4203-4204
22. Fowler F.W., Hassner A., and Levy L.A. J. Am. Chem. Soc. 89 (1967) 2077-2082
23. Kirschning A., Hashem M.A., Monenschein H., Rose L., and Schoning K.-U. J. Org. Chem. (1999) 6522-6526
24. Nair V., George T.G., Sheeba V., Augustine A., Balagopal L., and Nair L.G. Synlett (2000) 1597-1598
25. Barluenga J., Alvarez-Perez M., Fananas F.J., and Gonzales J.M. Adv. Synth. Catal. (2001) 335-337
26. Curini M., Epifano F., Marcotullio M.C., and Rosati O. Tetrahedron Lett. 43 (2002) 1201-1203
27. Hassner A., and Boerwinkle F. J. Am. Chem. Soc. 90 (1968) 216-218
28. Boerwinkle F., and Hassner A. Tetrahedron Lett. 9 (1968) 3921-3924
29. Hassner A., and Boerwinkle F. Tetrahedron Lett. 10 (1969) 3309-3312
30. Van Ende D., and Krief A. Angew. Chem., Int. Ed. Engl. 13 (1974) 279-280
31. Denis J.N., and Krief A. Tetrahedron 35 (1979) 2901-2903
32. Olah G.O., Wang Q., Li X.-Y., and Prakash G.K.S. Synlett (1990) 487-489
33. Hajra S., Sinha D., and Bhowmick M. Tetrahedron Lett. 47 (2006) 7017-7019
34. Hajra S., Bhowmick M., and Sinha D. J. Org. Chem. (2006) 9237-9240
35. Kharasch M.S., and Priestley H.N. J. Am. Chem. Soc. 61 (1939) 3425
36. Terauchi H., Kowata K., Minematsu T., and Takemura S. Chem. Pharm. Bull. 25 (1977) 556
37. Hegedus L.S., and McKearin J.M. J. Am. Chem. Soc. 104 (1982) 2444
38. Revesz L., Blum E., and Wicki R. Tetrahedron Lett. 46 (2005) 5577
39. Griffith D.A., and Danishefsky S.J. J. Am. Chem. Soc. 118 (1996) 9526
40. Shen R., and Huang X. J. Org. Chem. 72 (2007) 3961
41. Han J., Li T., Pan Y., Kattuboina A., and Li G. Chem. Biol. Drug. Des. 71 (2008) 71-77
42. Phukan P., Chakraborty P., and Kataki D. J. Org. Chem. 71 (2006) 7533-7537
43. Nair C.G.R., and Indrasen P. Talanta 23 (1976) 239
44. 3, 100 MHz) δ: 13.9, 29.7, 41.3, 53.3, 62.7.
45. Rodebaugh R., and Fraser-Reid B. Tetrahedron 52 (1996) 7663-7678