Synlett 2014; 25(14): 2075-2077
DOI: 10.1055/s-0034-1378449
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 7-Pentafluorophenyl-1H-indole: An Anion Receptor for Anion–π Interactions

Zhan-Hu Sun
a   Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092385   Email: markus.albrecht@oc.rwth-aachen.de
,
Markus Albrecht*
a   Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092385   Email: markus.albrecht@oc.rwth-aachen.de
,
Michael Giese
a   Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092385   Email: markus.albrecht@oc.rwth-aachen.de
,
Fangfang Pan
b   Department of Chemistry, Nanoscience Center, University of Jyväskylä, Survontie 9, 40014 Jyväskylä, Finland
c   Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Kari Rissanen
b   Department of Chemistry, Nanoscience Center, University of Jyväskylä, Survontie 9, 40014 Jyväskylä, Finland
› Author Affiliations
Further Information

Publication History

Received: 07 May 2014

Accepted after revision: 10 June 2014

Publication Date:
16 July 2014 (online)


Dedicated to Professor Yu Liu on the occasion of his 60th birthday

Abstract

7-Pentafluorophenyl-1H-indole has the potential to be a key compound for the investigation of anion–π interactions in solution. Unfortunately, it was not possible to obtain it by aryl–aryl coupling reaction. Finally, it has been prepared by Bartoli indole synthesis. The key compound as well as analogues were submitted to preliminary studies of anion binding. Single crystals of two key receptors were obtained.

 
  • References and Notes

    • 1a Ma JC, Dougherty DA. Chem. Rev. 1997; 97: 1303
    • 1b Zacharias N, Dougherty DA. Trends Pharmacol. Sci. 2002; 23: 281
  • 2 Mascal M, Armstrong A, Bartberger MD. J. Am. Chem. Soc. 2002; 124: 6274
    • 3a Quiñonero D, Garau C, Rotger C, Frontera A, Ballester P, Costa A, Deyà PM. Angew. Chem. Int. Ed. 2002; 41: 3389
    • 3b Alkorta I, Rozas I, Elguero J. J. Am. Chem. Soc. 2002; 124: 8593
    • 4a Schottel BL, Chifotides HT, Dunbar KR. Chem. Soc. Rev. 2008; 37: 68
    • 4b Estarellas C, Frontera A, Quinonero D, Deya PM. Angew. Chem. Int. Ed. 2011; 50: 415
    • 4c Hay BP, Bryantsev VS. Chem. Commun. 2008; 2417
    • 4d Frontera A, Gamez P, Mascal M, Mooibroek TJ, Reedijk J. Angew. Chem. Int. Ed. 2011; 50: 9564
  • 5 Ballester P. Acc. Chem. Res. 2013; 46: 874
  • 6 Berryman OB, Hof F, Hynes MJ, Johnson DW. Chem. Commun. 2006; 506
    • 7a Giles ID, Chifotides HT, Shatruk M, Dunbar KR. Chem. Commun. 2011; 47: 12604
    • 7b Chifotides HT, Dunbar KR. Acc. Chem. Res. 2013; 46: 894
    • 8a Wang DX, Zheng QY, Wang QQ, Wang MX. Angew. Chem. Int. Ed. 2008; 47: 7485
    • 8b Wang DX, Wang MX. J. Am. Chem. Soc. 2013; 135: 892
  • 9 de Hoog P, Gamez P, Mutikainen I, Turpeinen U, Reedijk J. Angew. Chem. Int. Ed. 2004; 43: 5815
  • 10 Dawson RE, Hennig A, Weimann DP, Emery D, Ravikumar V, Montenegro J, Takeuchi T, Gabutti S, Mayor M, Mareda J, Schalley CA, Matile S. Nat. Chem. 2010; 2: 533
  • 11 Gil-Ramirez G, Escudero-Adan EC, Benet-Buchholz J, Ballester P. Angew. Chem. Int. Ed. 2008; 47: 4114
  • 12 Adriaenssens L, Gil-Ramirez G, Frontera A, Quinonero D, Escudero-Adan EC, Ballester P. J. Am. Chem. Soc. 2014; 136: 3208
    • 13a Albrecht M, Wessel C, de Groot M, Rissanen K, Luchow A. J. Am. Chem. Soc. 2008; 130: 4600
    • 13b Albrecht M, Müller M, Mergel O, Rissanen K, Valkonen A. Chem. Eur. J. 2010; 16: 5062
    • 13c Giese M, Albrecht M, Krappitz T, Peters M, Gossen V, Raabe G, Valkonen A, Rissanen K. Chem. Commun. 2012; 48: 9983
  • 14 Bretschneider A, Andrada DM, Dechert S, Meyer S, Mata RA, Meyer F. Chem. Eur. J. 2013; 19: 16988
  • 15 Fanta PE. Chem. Rev. 1946; 38: 139
  • 16 Molander GA, Biolatto B. J. Org. Chem. 2003; 68: 4302
  • 17 Mentzel UV, Tanner D, Tonder JE. J. Org. Chem. 2006; 71: 5807
  • 18 Pummer WJ, Wall LA. Science 1958; 127: 643
  • 19 Bartoli G, Dalpozzo R, Nardi M. Chem. Soc. Rev. 2014; 43: 4728
    • 20a Bartoli G, Palmieri G, Bosco M, Dalpozzo R. Tetrahedron Lett. 1989; 30: 2129
    • 20b Xie K, Yang Z, Zhou X, Li X, Wang S, Tan Z, An X, Guo CC. Org. Lett. 2010; 12: 1564
  • 21 CCDC 1001536 (2) and 955438 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.