Grindstone chemistry: (Diacetoxyiodo)benzene-mediated oxidative nuclear halogenation of arenes using NaCl, NaBr or I2

Journal of Chemical Research

Volumn , Issue 6, 2006, Pages 366-368

  Karade, N N ^a   Tiwari, G B ^a   Huple, D B ^a   Siddiqui, T A J ^a  

^a SWAMI RAMANAND TEERTH MARATHWADA UNIVERSITY   (India)

Author keywords

(Diacetoxyiodo)benzene; Grindstone chemistry; Nuclear halogenation

Indexed keywords

EID: 33746106857     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823406777946761     Document Type: Article

References (58)

1. (a) C. Christophersen, Acta Chem. Scand. B, 1985, 39, 515;
2. (b) A. Butler and J.V. Walker, Chem. Rev., 1993, 93, 1937;
3. (c) K.C. Nicolaou, Angew. Chem. Int. Ed. Engl., 1993, 32, 1377.
4. (a) E. Negishi, C. Coperet, S. Ma, S. Liou and F. Liu, Chem. Rev., 1996, 96, 365;
5. (b) F. Diederich and P.J. Stang, Metal Catalysed Cross Coupling Reactions; Wiley-VCH: Weinheim, Germany, 1998.
6. For recent examples of chlorination and bromination protocols see: (a) K. Smith, M. Butters, W.E. Paget, D. Goubet, E. Fromentin and B. Nay, Green Chem., 1999, 1, 83;
7. (b) N.B. Barhate, A.S. Gajare, R.D. Wakharkar and A.V. Bedekar, Tetrahedron, 1999, 55, 11127;
8. (c) G. Rothenberg and J.H. Clark, Org. Proc. Res. Dev., 2000, 4, 270;
9. (d) U. Bora, G. Bose, M.K. Chaudhuri, S.S. Dhar, R. Gopinath, A. Khan and B.K. Patel, Org. Lett., 2000, 2, 247;
10. (e) N. Narender, K.V. V.K. Mohan, R.V. Reddy, P. Srinivasu, S.J. Kulkarni and K.V. Raghavan, J. Mol. Catal. A, 2003, 192, 73.
11. For recent examples of iodination protocols see: (a) T. Mukaiyama, H. Kitagawa and J. Matsuo, Tetrahedron Lett., 2000, 41, 9383;
12. (b) S.J. Garden, J.C. Torres, S.C. de Souza Melo, A.S. Lima, A.C. Pinto and E.L.S. Lima, Tetrahedron Lett., 2001, 42, 2089;
13. (c) A.S. Castanet, F. Colobert and P.E. Broutin, Tetrahedron Lett., 2002, 43, 5047;
14. (d) R.D. Tilve, V.M. Alexander and B.M. Khadilkar, Tetrahedron Lett., 2002, 43, 9457.
15. (a) V. Kavala, S. Naik and B.K. Patel, J. Org. Chem., 2005, 70, 4267;
16. (b) M.Y. Park, S.G. Yang, V. Jadhav and Y.H. Kim, Tetrahedron Lett., 2004, 45, 4887;
17. (c) M. Sosnowski, L. Skulski and K. Wolowik, Molecules, 2004, 9, 617;
18. (d) S.C. Roy, C. Guin, K.K. Rama and G. Maiti, Tetrahedron Lett., 2001, 42, 6941.
19. (a) H.M. Meshram, P.N. Reddy, K. Sadashiv and J.S. Yadav, Tetrahedron Lett., 2005, 46, 623;
20. (b) J.S. Yadav, B.V.S. Reddy, P.S.R. Reddy, A.K. Basak and A.V. Narsaiah, Adv. Synth. Catal., 2004, 346, 77;
21. (c) R.A. Day, J.A. Blake and C.E. Stephens, Synthesis, 2003, 10, 1586;
22. (d) M.C. Carreno, J.L. Garcia Ruano, G. Sanz, M.A. Toledo and A.J. Urbano, J. Org. Chem., 1995, 60, 5328.
23. (a) D. Bogdal, M. Lukasiewicz and J. Pielichowski, Green Chem., 2004, 6, 110;
24. (b) S.C. Roy, C. Guin, K.K. Rana and G. Maiti, Tetrahedron Lett., 2001, 42, 6941;
25. (c) D. Roche, K. Prasad, O. Repic and T.J. Blacklock, Tetrahedron Lett., 2000, 41, 2083;
26. (d) M. Zupan, J. Iskra and S. Stavber, Tetrahedron Lett., 1997, 38, 6305;
27. (e) S.C. Roy, C. Guin, K.K. Rana and G. Maiti, Tetrahedron Lett., 2001, 42, 6941.
28. (a) T. Anastas and J.C. Warner, Green Chemistry: Theory and Practice. Oxford Science Publications, New York, 1998;
29. (b) K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025;
30. (c) M. Eissen, J.O. Metzger, E. Schmidt and U. Schneidewind, Angew. Chem. Int. Ed., 2002, 41, 414.
31. (a) R.M. Moriarty, J. Org. Chem., 2005, 70, 2893;
32. (b) T. Wirth, Angew Chem. Int. Ed., 2005, 44, 3656;
33. (c) P.J. Stang, J. Org. Chem., 2003, 68, 2997;
34. (d) V.V. Zhdankin and P.J. Stang, Chem. Rev., 2002, 102, 2523.
35. (a) A. Varvoglis, Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997, pp 6;
36. (b) A. Varvoglis and S. Spyroudis, Synlett, 1997, 221.
37. (a) H.S. Rho, B-S Ko, H.K. Kim and Y-S. Ju, Synth. Commun. 2002, 32, 1303;
38. (b) P.A. Evans, J.D. Nelson and T. Manangan, Synlett, 1997, 968;
39. P.A. Evans and T.A. Brandt, J. Org. Chem., 1997, 62, 5321.
40. (a) E.B. Merkushev, N.D. Simakhina and G.M. Koveshnikova, Synthesis, 1980, 486;
41. (b) M. D'Auria and G. Mauriello, Tetrahedron Lett., 1995, 36, 4883;
42. (c) B. Panunzi, L. Ritiroti and M. Tingoli, Tetrahedron Lett., 2003, 44, 8753.
43. (a) R. Neu, Ber. Deutsch. Chem. Ges., 1939, 72, 1505;
44. (b) V.G. Kostina, E.K. Rutkovskii and N.G. Feshchenko, Zh. Obsch. Khim., 1984, 54, 1001.
45. (a) A.K. Bose, S. Pednekar, S.N. Ganguly, G. Chakraborty and M.S. Manhas, Tetrahedron Lett., 2004, 45, 8351;
46. (b) J.N. Moorthy, N. Singhal and P. Venkatakrishnan, Tetrahedron Lett., 2004, 45, 5419;
47. (c) V.K. Balema, J.W. Wiench, M. Pruski and V.K. Pecharsky, J. Am. Chem. Soc., 2002, 124 (22), 6244;
48. (d) J.L. Scott and C.L. Raston, Green Chem., 2000, 2, 245;
49. (e) F. Toda, T. Suzuki and S. Higa, J. Chem. Soc. Perkin Trans. 1, 1998, 3521.
50. F. Toda, K. Tanaka and A. Sekikawa, J. Chem. Soc., Chem. Commun., 1987, 279.
51. (a) N.N. Karade, G.B. Tiwari and D.B. Huple, Synlett, 2005, 13, 2039;
52. (b) N.N. Karade, S.G. Shirodkar, B.M. Dhoot and P.B. Waghmare, J. Chem. Res.(S), 2005, 4, 274;
53. (c) N.N. Karade, G.B. Tiwari, S.G. Shirodkar and B.M. Dhoot, Synth. Commun., 2005, 35, 1197;
54. (d) N.N. Karade, S.G. Shirdokar, M.N. Patil, R.A. Potrekar and H.N. Karade, Tetrahedron Lett., 2003, 44, 6729.
55. S.M. Hubig, W. Jung and J.K. Kochi, J. Org. Chem., 1994, 59, 6233.
56. (a) Dictionary of Organic Compounds, Chapman & Hall: London, 6th edn, 1996;
57. (b) Aldrich Catalogue of Chemicals, 2003.
58. A. Bachki, F. Foubelo and M. Yus, Tetrahedron, 1994, 50, 5139.