Regioselective iodination of phenol and analogues using N-iodosuccinimide and p-toluenesulfonic acid

Tetrahedron Letters

Volumn 50, Issue 22, 2009, Pages 2664-2667

  Bovonsombat, Pakorn ^a   Leykajarakul, Juthamard ^a   Khan, Chiraphorn ^a   Pla on, Kawin ^a   Krause, Michael M ^a   Khanthapura, Pratheep ^a   Ali, Rameez ^a   Doowa, Niran ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

N IODOSUCCINIMIDE; PHENOL; PHENOL DERIVATIVE; SUCCINIMIDE; SULFONIC ACID DERIVATIVE; TOLUENESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; IODINATION; ROOM TEMPERATURE; STOICHIOMETRY;

EID: 64549113446     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.128     Document Type: Article

References (49)

1. Merkushev E.B. Synthesis (1988) 923-937
2. Georgiades S.N., and Clardy J. Org. Lett. 8 (2006) 4251-4254
3. Heck R.F. Org. React. 27 (1982) 345-390
4. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508-524
5. Suzuki A., and Miyaura N. Chem. Rev. 95 (1995) 2457-2483
6. Ma D., and Cai Q. Acc. Chem. Res. 41 (2008) 1450-1460
7. Fusetani N., and Matsunaga S. Chem. Rev. 93 (1993) 1793-1806
8. Lista L., Pezzella A., Napolitano A., and d'Ischia M. Tetrahedron 64 (2007) 234-239
9. Johnsson R., Meijer A., and Ellervik U. Tetrahedron 61 (2005) 11657-11663
10. Yang S.G., and Kim Y.H. Tetrahedron Lett. 40 (1999) 6051-6054
11. Brunel Y., and Rousseau G. Tetrahedron Lett. 36 (1995) 8217-8220
12. Kajigaeshi S., Kakinami T., Yamasaki H., Fujisaki S., Kondo M., and Okamoto T. Chem. Lett. (1987) 2109-2112
13. Kometani T., Watt D.S., and Ji T. Tetrahedron Lett. 26 (1985) 2043-2046
14. Kometani T., Watt D.S., Ji T., and Fritz T. J. Org. Chem. 50 (1985) 5384-5387
15. Das B., Krishnaiah M., Venkateswarlu K., and Reddy V.S. Tetrahedron Lett. 48 (2007) 81-83
16. Veglia A.V., and De Rossi R.H. J. Org. Chem. 53 (1988) 5281-5287
17. Cambie R.C., Rutledge P.S., Smith-Palmer T., and Woodgate P.D. J. Chem. Soc., Perkin Trans. 1 (1976) 1161-1164
18. Hajipour A.R., and Adibi H. J. Chem. Res. (2004) 294-295
19. Olah G.A., Wang Q., Sanford G., and Surya Prakash G.K. J. Org. Chem. 58 (1993) 3194-3195
20. Bovonsombat P., Angara G.J., and McNelis E. Synlett (1992) 131-132
21. Bovonsombat P., and McNelis E. Synthesis (1993) 237-241
22. Carreño M.C., García Ruano J.L., Sanz G., Toledo M.A., and Urbano A. J. Org. Chem. 60 (1995) 5328-5331
23. Carreño M.C., García Ruano J.L., Sanz G., Toledo M.A., and Urbano A. Tetrahedron Lett. 37 (1996) 4081-4084
24. Castanet A.-S., Colobert F., and Broutin P.-E. Tetrahedron Lett. 43 (2002) 5047-5048
25. Bovonsombat P., Khanthapura P., Krause M.M., and Leykajarakul J. Tetrahedron Lett. 49 (2008) 7008-7011
26. Wohlleben W.J. Ber. Dtsch. Chem. Ges. 42 (1910) 4369-4375
27. Woo L.W.L., Bubert C., Sutcliffe O.B., Smith A., Surinder K.C., Mahon M.F., Purohit A., Reed M.J., and Potter B.V.L. J. Med. Chem. 50 (2007) 3540-3560
28. Pearson D.E., Frazer M.G., Frazer V.S., and Washburn L.C. Synthesis (1976) 621-623
29. Tassilly E., and Leroide J. Bull. Soc. Chim. Fr. 3 (1908) 124-126
30. Chang C.T., Chen F.C., Chen T.S., Hsu K.K., Ueng T., and Hung M. J. Chem. Soc. (1961) 3414-3417
31. Cassebaum H., and Herzberg H. Z. Chem. 16 (1976) 319-320
32. Brazier S.A., and McCombie H. J. Chem. Soc., Trans. 101 (1912) 968-977
33. King G., and McCombie H. Proc. Chem. Soc. 29 (1913) 8-9
34. Bogdal D., Lukasiewicz M., and Pielichowski J. Green Chem. 6 (2004) 110-113
35. Edgar K.J., and Falling S.N. J. Org. Chem. 55 (1990) 5287-5291
36. +), 74 (2), 65 (23), 53 (3), 39 (10).
37. +), 77 (28), 63 (3), 51 (9), 39 (3).
38. +), 77 (34), 63 (4), 51 (7), 39 (4).
39. +), 94 (2), 80 (5), 79 (5), 63 (5), 52 (11).
40. +), 127 (3, I), 120 (7), 107 (3), 92 (12), 77 (5), 63 (12), 43 (12).
41. +), 127 (3, I), 120 (3), 119 (3), 92 (8), 91 (9), 63 (22), 53 (8), 38 (2).
42. +), 99 (21), 91 (10), 73 (8), 63 (21).
43. +), 53 (5).
44. +), 101 (7), 99 (23), 73 (7), 63 (15), 53 (4).
45. +), 145 (11), 143 (12), 127 (7, I), 119 (3), 117 (3), 92 (19), 74 (3), 63 (28), 53 (8), 38 (3).
46. +), 127 (2, I), 115 (36), 89 (4), 74 (2), 63 (5) 39 (1).
47. +), 135 (5), 127 (3, I), 115 (52), 89 (7), 63 (7), 32 (5).
48. Sket B., Zupet P., and Zupan M. J. Chem. Soc., Perkin Trans. 1 (1989) 2279-2281
49. 1H NMR and MS data of 11a matched those reported in the literature