Synthesis 2015; 47(24): 3901-3906
DOI: 10.1055/s-0035-1560480
paper
© Georg Thieme Verlag Stuttgart · New York

Clean and Efficient Iodination of Thiophene Derivatives

Jérémie Grolleau
University of Angers, MOLTECH-Anjou UMR CNRS 6200, SCL group, 2 boulevard Lavoisier, 49045 Angers cedex, France   Email: frederic.gohier@univ-angers.fr
,
Pierre Frère
University of Angers, MOLTECH-Anjou UMR CNRS 6200, SCL group, 2 boulevard Lavoisier, 49045 Angers cedex, France   Email: frederic.gohier@univ-angers.fr
,
Frédéric Gohier*
University of Angers, MOLTECH-Anjou UMR CNRS 6200, SCL group, 2 boulevard Lavoisier, 49045 Angers cedex, France   Email: frederic.gohier@univ-angers.fr
› Author Affiliations
Further Information

Publication History

Received: 26 June 2015

Accepted after revision: 26 August 2015

Publication Date:
11 September 2015 (online)


Abstract

Iodination of thiophene derivatives is realized using a simple, fast, and efficient methodology. Iodination of thiophene and 2- or 3-substituted or 3,4-disubstituted thiophenes with N-iodosuccinimide (NIS) activated with 4-toluenesulfonic acid in ethanol gives pure iodinated products that require no further purification.

Supporting Information

Primary Data

 
  • References

  • 1 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
  • 2 Bakherad M. Appl. Organomet. Chem. 2013; 27: 125
  • 3 Strappaveccia G, Ismalaj E, Petrucci C, Lanar D, Marrocchi A, Drees M, Facchetti A, Vaccaro L. Green Chem. 2015; 17: 365
  • 4 Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
    • 5a Heinrich AC. J, Thiedemann B, Gates PJ, Staubitz A. Org. Lett. 2013; 15: 4666
    • 5b Fin A, Jentzsch AV, Sakai N, Matile S. Angew. Chem. Int. Ed. 2012; 51: 12736
  • 6 Marzano G, Ciasca CV, Babudri F, Bianchi G, Pellegrino A, Po R, Farinola GM. Eur. J. Org. Chem. 2014; 6583
  • 7 Burke DJ, Lipomi DJ. Energy Environ. Sci. 2013; 6: 2053
    • 8a Arsenyan P, Paegle E, Belyakov S. Tetrahedron Lett. 2010; 51: 205
    • 8b Goldberg Y, Alper H. J. Mol. Catal. 1994; 88: 377
  • 9 Kraszkiewicz L, Sosnowski M, Skulski L. Synthesis 2006; 1195
  • 10 Krassowska-Swiebocka B, Lulinski P, Skulski L. Synthesis 1995; 926
  • 11 Lulinski P, Krassowska-Swiebocka B, Skulski L. Molecules 2004; 9: 595 ; http://www.mdpi.com/journal/molecules
  • 12 Sosnowski M, Skulski L. Molecules 2005; 10: 401 ; http://www.mdpi.com/journal/molecules
  • 13 Lulinski P, Skulski L. Bull. J. Chem. Soc. Jpn. 1997; 70: 1665
  • 14 L’Helgoual’ch JM, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F. J. Org. Chem. 2008; 73: 177
  • 15 Prakash GK. S, Mathew T, Hoole D, Esteves PM, Wang Q, Rasul G, Olah GA. J. Am. Chem. Soc. 2004; 126: 15770
  • 16 Yamamoto T, Toyota K, Morita N. Tetrahedron Lett. 2010; 51: 1364
  • 17 Bailey L, Handy ST. Tetrahedron Lett. 2011; 52: 2413
    • 18a Fisyuk AS, Bogza YP, Belyaeva LV, Belyaev VB. Chem. Heterocycl. Compd. 2012; 48: 1078
    • 18b Jacobson KA, Shi D, Gallo-Rodriguez C, Manning MJr, Müller C, Daly JW, Neumeyer JL, Kiriasis L, Pfleiderer W. J. Med. Chem. 1993; 36: 2639
    • 18c Ryabova V, Ignatovich L. Thiophenes . In Topics in Heterocyclic Chemistry . Vol. 39. Joule JA. Springer; Heidelberg: 2014: 74
  • 19 Cardolaccia T, Funston AM, Kose ME, Keller JM, Miller JR, Schanze KS. J. Phys. Chem. B 2007; 111: 10871
  • 20 Bayh O, Awad H, Mongin F, Hoarau C, Trecourt F, Queguiner G, Marsais F, Blanco F, Abarca B, Ballesteros R. Tetrahedron 2005; 61: 4779
  • 21 Ashizawa M, Niimura T, Yu Y, Tsuboi K, Matsumoto H, Yamada R, Kawauchi S, Tanioka A, Mori T. Tetrahedron 2012; 68: 2790
  • 22 Notaras EG. A, Lucas NT, Humphrey MG, Willis AC, Rae AD. Organometallics 2003; 22: 3659
  • 23 Guilard R, Fournari P, Person M. Bull. Soc. Chim. Fr. 1967; 11: 4121
  • 24 Onys’ko PP, Kim TV, Kiseleva OI, Rassukana YV, Gakh AA. J. Fluorine Chem. 2009; 130: 501
  • 25 Muehlhausen U, Schirrmacher R, Piel M, Lecher B, Briefert M, Piee-Staffa A, Kaina B, Roesch F. J. Med. Chem. 2006; 49: 263
  • 26 Miller LL, Yu Y. J. Org. Chem. 1995; 60: 6813
  • 27 Tam IW, Yan J, Breslow R. Org. Lett. 2006; 8: 183
  • 28 Ishii A, Kobayashi S, Aoki Y, Annaka T, Nakata N. Heteroat. Chem. 2014; 25: 658
  • 29 Wonneberger H, Ma CQ, Gatys MA, Li C, Bauerle P, Mullen K. J. Phys. Chem. B 2010; 114: 14343
  • 30 L’Helgoual’ch JM, Bentabed-Ababsa G, Chevallier F, Yonehara M, Uchiyama M, Derdour A, Mongin F. Chem. Commun. 2008; 5375
  • 31 Karlsson JO, Svensson A, Gronowitz S. J. Org. Chem. 1984; 49: 2018
  • 32 Meng Q, Gao JH, Li RJ, Jiang L, Wang CL, Zhao HP, Liu CM, Li HX, Hu WP. J. Mater. Chem. 2009; 19: 1477
  • 33 Gupta A, Ali A, Bilic A, Gao M, Hegedus K, Singh B, Watkins SE, Wilson GJ, Bach U, Evans RA. Chem. Commun. 2012; 48: 1889
  • 34 Jessing M, Brandt M, Jensen KJ, Christensen JB, Boas U. J. Org. Chem. 2006; 71: 6734
  • 35 Li ZH, Wong MS, Fukutani H, Tao Y. Chem. Mater. 2005; 17: 5032