Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH13324
RESEARCH ARTICLE
Contents Vol 66(12)

A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination Strategy

Raed M. Al-Zoubi A C , Hassan Abul Futouh A and Robert McDonald B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid, 22110, Jordan.

B Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Alberta, T6G2G2, Canada.

C Corresponding author. Email: rmzoubi@just.edu.jo

Australian Journal of Chemistry 66(12) 1570-1575 https://doi.org/10.1071/CH13324
Submitted: 25 June 2013  Accepted: 20 August 2013   Published: 25 September 2013

Abstract

A mild and convenient synthesis of 1,2,3-triiodoarenes has been developed. This method consists of two steps which can be performed on multigram scale with moderate to excellent yields. This report discloses a practical synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, operationally simple, scalable, and is easy to workup and to purify. We also report the first regioselective transmetalation reaction of 1,2,3-triiodoarenes to provide ortho-diiodoaryl derivatives, which are useful building blocks and indeed are hard to make by other means.


References

[1]  L. Koehler, K. Gagnon, S. McQuarrie, F. Wuest, Molecules 2010, 15, 2686.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXltFygsr4%3D&md5=f34f98d88031b4ab652471cf1a0c57f7CAS | 20428073PubMed |

[2]  (a) S. J. Blanksby, G. B. Ellison, Acc. Chem. Res. 2003, 36, 255.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXmt1OqsA%3D%3D&md5=a481ac44ab1af0f3a12ba3d087a5658dCAS | 12693923PubMed |
         (b) P. Knochel, Handbook of Functionalized Organometallics 2004 (Wiley-VCH: Weinheim).

[3]  (a) E. B. Merkushev, Synthesis 1998, 923.
      (b) J. R. Hanson, J. Chem. Res. 2006, 277.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Stavber, M. Jereb, M. Zupan, Synthesis 2008, 1487.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) G. C. Clososki, C. J. Rohbogner, P. Knochel, Angew. Chem. Int. Ed. 2007, 46, 7681.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1Sis7%2FJ&md5=5c079c299d7a4eaa8cd77c1716898dddCAS |
      (b) S. Usui, Y. Hashimoto, J. V. Morey, A. E. H. Wheatley, M. Uchiyama, J. Am. Chem. Soc. 2007, 129, 15102.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. Dolenc, B. Plesnicar, J. Org. Chem. 2006, 71, 8028.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) E. F. Perozzi, R. S. Michalak, G. D. Figuly, W. H. Stevenson, D. Dess, M. R. Ross, J. C. Martin, J. Org. Chem. 1981, 46, 1049.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) N. Meyer, D. Seebach, Chem. Ber. 1980, 113, 1304.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  J. Cvengroš, D. Stolz, A. Togni, Synthesis 2009, 2009, 2818.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  R. Johnsson, A. Meijer, U. Ellervik, Tetrahedron 2005, 61, 11657.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtF2ru77F&md5=8d2be43e6de44615569e0930bf390458CAS |

[7]  (a) D. Manna, G. Mugesh, J. Am. Chem. Soc. 2011, 133, 9980.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXnt12nsbs%3D&md5=6423b7be0ef58e269e1106cc786efed6CAS | 21648483PubMed |
      (b) P. R. Larsen, M. J. Berry, Annu. Rev. Nutr. 1995, 15, 323.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. J. Berry, L. Banu, P. R. Larsen, Nature 1991, 349, 438.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) D. Behne, A. Kyriakopoulos, H. Meinhold, J. Köhrle, Biochem. Biophys. Res. Commun. 1990, 173, 1143.
         | Crossref | GoogleScholarGoogle Scholar |
         (e) J. L. Leonard, T. J. Visser, In Thyroid Hormone Metabolism (Ed. G. Hennemann) 1986, p. 189 (Marcel Dekker: New York, NY).

[8]  (a) S.-B. Yu, A. D. Watson, Chem. Rev. 1999, 99, 2353.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXltVGhsrw%3D&md5=2e67f329c7dde1f259d6cb69e25d90e5CAS | 11749484PubMed |
      (b) W. A. Volkert, T. J. Hoffman, Chem. Rev. 1999, 99, 2269.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) D. L. Mattern, X. Chen, J. Org. Chem. 1991, 56, 5903.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXlsFylsb8%3D&md5=659e9e2657a285e56c679ef24323c215CAS |
      (b) J. Arotsky, R. Butler, A. C. Darby, J. Chem. Soc. 1970, 1480.

[10]  (a) T. Sato, S. Shimada, K. Hata, Bull. Chem. Soc. Jpn. 1971, 44, 2484.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXlsFWmu74%3D&md5=70321bb0a583c1a435ba4517986e7ba5CAS |
      (b) L. Kalb, F. Schweizer, H. Zellner, E. Berthold, Chem. Ber. 1926, 59, 1860.
      (c) C. Willgerodt, E. Arnold, Chem. Ber. 1901, 34, 3343.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  M. B. Smith, L. Guo, S. Okeyo, J. Stenzel, J. Yanella, E. LaChapelle, Org. Lett. 2002, 4, 2321.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XktlCgt74%3D&md5=1471c0ece4e09ed91a5a421d1761da50CAS | 12098237PubMed |

[12]  (a) V. K. Chaikovski, T. S. Kharlova, V. D. Filimonov, T. A. Saryucheva, Synthesis. 1999, 1999, 748.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) A. Bachki, F. Foubelo, M. Yus, Tetrahedron 1994, 50, 5139.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) W.-W. Sy, B. A. Lodge, A. W. By, Synth. Commun. 1990, 20, 877.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) C. Galli, Chem. Rev. 1988, 88, 765.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXkslejtL0%3D&md5=90d2b1606206eea50f5054e398b177c1CAS |
      (b) T. I. Godovikova, O. A. Rakitin, L. I. Khmelnitskii, Russ. Chem. Rev. 1983, 52, 440.
         | Crossref | GoogleScholarGoogle Scholar |
         (c) S. Patai, The Chemistry of Diazonium and Diazo Groups 1978 (Wiley: New York, NY).

[14]  (a) E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis 2007, 81.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1Wisro%3D&md5=a2dbdf5f6ed1f22de11fcff54df3bef8CAS |
      (b) W.B. Smith, O. C. Ho, J. Org. Chem. 1990, 55, 2543.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) L. Friedman, J. Chlebowski, J. Org. Chem. 1968, 33, 1636.

[15]  CCDC-907172 contains the supplementary crystallographic data for compound 18. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.