Direct One Pot Synthesis of Iodoarenes from Aromatic Amine Using TCT-Wet.Sio2 as an Effective Heterogeneous Catalyst

Authors

  • Somnath S. Gholap  Post graduate Department and Research Centre, Padmashri Vikhe Patil College, Pravaranagar (Loni Kd.), Rahata, Ahmednagar, India

Keywords:

Trichlorotriazene, diazonium salt, HCl

Abstract

The present article described the one pot direct synthesis of structurally diverse aryl iodides from primary aromatic amines in aprotic media. 1,3,5-Trichlorotriazene (TCT)-Wet. SiO2 (50 % W/W) was found to be an effective heterogeneous catalyst for in situ generation of diazonium salt followed by iodination with potassium iodide. The methodology presented here was worked well for the variety of aromatic amines possessing electron donating as well as electron withdrawing substituents on aromatic ring at room temperature. The corresponding aryl iodides are obtained in good to excellent yield.

References

  1. a) P.E. Fanta, Synlett., 1974, 9; b) M. Nilsson, Tetrahedron Lett., 1966, 679; c) H.O. House, W.L. Resress, G.M. Whiteside, J. Org. Chem., 1966, 31, 3128; d) H. Suzuki, H. Abe, A. Osuka,? Chem. Lett., 1980, 1363.
  2. a) W.A. Volkert, T.J. Hofmann, Chem. Rev., 1999, 99, 2269; b) S.B. Yu, A.D. Watson, Chem. Rev., 1999, 99, 2353.
  3. For review see E.B. Merkushev, Synthesis, 1988, 923.
  4. T. Mukaiyama, H. Kitagawa, J.-I. Matsuo, Tetrahedron Lett., 2000, 41, 9383-9386.
  5. F. Radner,? J. Org. Chem., 1988, 53, 3548.
  6. a) T. Sugita, M. Idei, Y. Ishibashi, Y. Takegami, Chem. Lett. 1982, 1481; b) S. Umemura, A. Onoe, M. Okano, Bull. Chem. Soc. Jpn., 1974, 47, 147.
  7. a) H.O. Wirth, O. Konigslen, W. Kern, Liebigs Ann. Chem, 1960, 634, 84; b) S. Ahmad, et al Tetrahedron, 1976, 32, 503; c) Y. Ogata, K. Nakajima, Tetrahedron, 1964, 20, 43; d) J. Janssen, C.V. Wilson, Org. Synth, 1963, 547; e) L. Keefer, L. Andrews, J. Am. Chem. Soc. 1956, 78, 5623.
  8. Singh, R. P. and Kumar, R. Tetrahedron Lett. 1972, 7, 1972.
  9. (a) S. Patal In The Chemistry of Diazonium and Diazogroups, Ed; Wiley: NewYork, 1978; b) T.I Godovikova, O.A. Rakitin, L.I. Khmelnitskii, Russ. Chem. Rev. 1983, 52, 440.
  10. E.A. Krasnokutskaya? et al Synthesis, 2007, 1, 81-84.
  11. C. Galli, Chem. Rev., 1988, 88, 765.
  12. W.Baik, W. Laun, H. J. Lee, C. H. Yoon, B. H. Kim, Can. J. Chem. 2005, 83, 213.
  13. F. Nemati, A. Elhampour, Scientia Iranica 2012, 19(6), 1594-1596.
  14. M. E. Trusova, E.A. Krasnokutskaya, P. S. Postnikov,? Y. Choi, K.-W. Chi, V.D. Filimonov, Synthesis, 2011, 13, 2154-2158 ().
  15. E.A. Krasnokutskaya, N.I. Semenischeva, V.D. Filimonov, P. Knochel, Synthesis, 2007, 1,? 81-84.
  16. V. D. Filimonov, N. I. Semenischeva, E. A. Krasnokutskaya, A. N. Tretyakov, H.Y. Hwang, K.-W. Chi, Synthesis, 2008, 2, 185-187.
  17. D. A. Gorlushko, V. D. Filimonov, E. A. Krasnokutskaya, N. I. Semenischeva, B. S. Go, H.Y. Hwang, E. H. Cha, K.-Wh. Chi, Tetrahedron Lett., 2008, 49, 1080-1082.
  18. a) S. S.Gholap, S. R. Ugale, ChemistrySelect, 2017, 2(24), 7445-7449; b) S. S.Gholap, S. R.Ugale, Chem. Pap. 2017. Doi:10.1007/s11696-017-0237-1; c) S. S.Gholap, N. Gunjal, Arabian. J. Chem. 2017, 10, S2750-S2753; d) S. S.Gholap, Y. R. Sadaphal, Sensors and Actuators B. 2017, 253, 173-179; e) S. S. Gholap, Eur. J. Med. Chem. 2016, 110, 13-31; f) S. S. Gholap, Gunjal, N. Iranian J. Catal. 2016, 8, 147-152; g) S. S.Gholap, V. D. Dhakane, U. P. Deshmukh, H. V. Chavan, B. P. Bandgar, C R Chim 2014, 17, 431-436; h) S. S. Gholap, U. P. Deshmukh, Iranian J. Catal. 2013, 3, 171-176; i) S. S. Gholap, V. D. Dhakane, Sandeep S. Gholap, Jordon J. Chem. 2012, 7(3), 279-285; j) S. S. Gholap, V. D. Dhakane, S. N. Shelke, M. S. Tambe, Bull. Catal. Soc. India 2012, 11, 50; k) S. S. Gholap, Heterocycl Lett. 2012, 2(3), 461; l) S. S. Gholap, C. H. Gill, G. R. Pandhare, Indian J. Heterocycl. Chem. 2009, 18, 279.
  19. M. Shrama, S. Pandey, K. Chauvan, D. Shrma, B. Kumar, P.M.S.Chauvan, J. Org. Chem, 2012, 77, 929-937.
  20. M.A. Bigdeli, G. H.Mahdavinia, S. Jafari, H. Hazarkhani, Catal.Commun., 2007, 8, 2229-2231.

International Journal of Scientific Research in Science and Technology

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Published

2017-12-15

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Volume 3, Issue 9, November-December-2017

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Research Articles

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How to Cite

[1]
Somnath S. Gholap, " Direct One Pot Synthesis of Iodoarenes from Aromatic Amine Using TCT-Wet.Sio2 as an Effective Heterogeneous Catalyst, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 3, Issue 9, pp.297-300, November-December-2017.