Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

Tetrahedron Letters

Volumn 55, Issue 13, 2014, Pages 2154-2156

  Bose, Anima ^a   Mal, Prasenjit ^a  

^a NATIONAL INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

Aryl halogenation; Ball milling; Mechanochemistry; N halosuccinimide; Solvent free

Indexed keywords

AMMONIUM NITRATE; CERIC AMMONIUM NITRATE; N HALOSUCCINIMIDE DERIVATIVE; SUCCINIMIDE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG; N HALOSUCCINIMIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; BALL MILLING; BROMINATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; ELECTRON TRANSPORT; HALOGENATION; IODINATION; REACTION ANALYSIS; RECYCLING; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS; CATALYST; ELECTROPHILICITY;

EID: 84896520847     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.02.064     Document Type: Article

References (37)

1. Nonappa, K. Ahonen, M. Lahtinen, and E. Kolehmainen Green Chem. 13 2011 1203 1209
2. R.B.N. Baig, and R.S. Varma Chem. Soc. Rev. 41 2012 1559 1584
3. G.W. Gribble Chem. Soc. Rev. 28 1999 335 346
4. P.S. Varma, and T.S. Subrahmanian J. Indian Chem. Soc. 13 1936 192 193
5. C. Djerassi Chem. Rev. 43 1948 271 317
6. M.C. Carreno, J.L. Garcia Ruano, G. Sanz, M.A. Toledo, and A. Urbano J. Org. Chem. 60 1995 5328 5331
7. J. Duan, L.H. Zhang, and W.R. Dolbier Jr. Synlett 1999 1245 1246
8. G.K.S. Prakash, T. Mathew, D. Hoole, P.M. Esteves, Q. Wang, G. Rasul, and G.A. Olah J. Am. Chem. Soc. 126 2004 15770 15776
9. G.K. Imanzadeh, M.R. Zamanloo, H. Eskandari, and K. Shayesteh J. Chem. Res. 2006 151 153
10. A. Chakradhar, R. Roopa, K.C. Rajanna, and P.K. Saiprakash Synth. Commun. 39 2009 1817 1824
11. M.C. Carreño, J. García Ruano, G. Sanz, M.A. Toledo, and A. Urbano Tetrahedron Lett. 37 1996 4081 4084
12. H. Wu, and J. Hynes Org. Lett. 12 2010 1192 1195
13. G.A. Olah, Q. Wang, G. Sandford, and G.K.S. Prakash J. Org. Chem. 58 1993 3194 3195
14. C.-Y. Zhou, J. Li, S. Peddibhotla, and D. Romo Org. Lett. 12 2010 2104 2107
15. Y.-L. Ren, H. Shang, J. Wang, X. Tian, S. Zhao, Q. Wang, and F. Li Adv. Synth. Catal. 355 2013 3437 3442
16. A. Stolle, T. Szuppa, S.E.S. Leonhardt, and B. Ondruschka Chem. Soc. Rev. 40 2011 2317 2329
17. G.-W. Wang Chem. Soc. Rev. 42 2013 7668 7700
18. S.L. James, C.J. Adams, C. Bolm, D. Braga, P. Collier, T. Friscic, F. Grepioni, K.D.M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A.G. Orpen, I.P. Parkin, W.C. Shearouse, J.W. Steed, and D.C. Waddell Chem. Soc. Rev. 41 2012 413 447
19. G.-W. Wang, and J. Gao Green Chem. 14 2012 1125 1131
20. R. Schmidt, A. Stolle, and B. Ondruschka Green Chem. 14 2012 1673 1679
21. J.N. Moorthy, P. Mal, R. Natarajan, and P. Venugopalan J. Org. Chem. 66 2001 7013 7019
22. The milling apparatus was stopped and small portion of the sample was collected from the reaction jar to study either TLC/ proton NMR. After this action, the reaction was started again and this operation time was excluded for reporting the reaction timing.
23. S. Duan, J. Turk, J. Speigle, J. Corbin, J. Masnovi, and R.J. Baker J. Org. Chem. 65 2000 3005 3009
24. R.E. Pearson, and J.C. Martin J. Am. Chem. Soc. 85 1963 354 355
25. A.V. Joshi, M. Baidossi, S. Mukhopadhyay, and Y. Sasson Org. Process Res. Dev. 8 2004 568 570
26. M.B. Smith, L. Guo, S. Okeyo, J. Stenzel, J. Yanella, and E. LaChapelle Org. Lett. 4 2002 2321 2323
27. G.-J.M. Gruter, O.S. Akkerman, and F. Bickelhaupt J. Org. Chem. 59 1994 4473 4481
28. D. Kikuchi, S. Sakaguchi, and Y. Ishii J. Org. Chem. 63 1998 6023 6026
29. J.N. Moorthy, P. Mal, N. Singhal, P. Venkatakrishnan, R. Malik, and P. Venugopalan J. Org. Chem. 69 2004 8459 8466
30. I.R.L. Barker, and R.H. Dahm J. Chem. Soc. B 1970 650
31. T. Kamei, H. Shibaguchi, M. Sako, K. Toribatake, and T. Shimada Tetrahedron Lett. 53 2012 3894 3896
32. P. Bovonsombat, J. Leykajarakul, C. Khan, K. Pla-on, M.M. Krause, P. Khanthapura, R. Ali, and N. Doowa Tetrahedron Lett. 50 2009 2664 2667
33. R.S. Neale, R.G. Schepers, and M.R. Walsh J. Org. Chem. 29 1964 3390 3393
34. V. Nair, L. Balagopal, R. Rajan, and J. Mathew Acc. Chem. Res. 37 2003 21 30
35. L. Wang, H. Jing, X. Bu, T. Chang, L. Jin, and Y. Liang Catal. Commun. 8 2007 80 82
36. B.R. Kim, E.J. Kim, G.H. Sung, J.-J. Kim, D.-S. Shin, S.-G. Lee, and Y.-J. Yoon Eur. J. Org. Chem. 2013 2013 2788 2791
37. D. Pla, F. Albericio, and M. Álvarez Eur. J. Org. Chem. 2007 1921 1924