Synthesis 2014; 46(11): 1448-1454
DOI: 10.1055/s-0033-1341249
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Preparation of Aromatic Triazenes and Their Application in Silver-Mediated Perfluoroalkylation Reactions

Andreas Hafner
a  Institute of Organic Chemistry, KIT-Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Fax: +49(721)60848581   Email: braese@kit.edu
,
Christoph Hussal
a  Institute of Organic Chemistry, KIT-Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Fax: +49(721)60848581   Email: braese@kit.edu
,
Stefan Bräse*
a  Institute of Organic Chemistry, KIT-Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Fax: +49(721)60848581   Email: braese@kit.edu
b  Institute of Toxicology and Genetics, KIT, Campus-North, Hermann-von-Helmholtz Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
› Author Affiliations
Further Information

Publication History

Received: 02 April 2014

Accepted after revision: 04 April 2014

Publication Date:
30 April 2014 (eFirst)

Abstract

Herein, the syntheses of various functionalized 1,3-diisopropyltriaz-1-enes is described. This simple transformation tolerates a vast number of functional groups (e.g., halides) and allows the syntheses of 1,3-diisopropyltriaz-1-enes starting from commercially available aniline derivatives. These substrates are suitable for a range of silver-mediated perfluoroalkylation reactions.

 
  • References

    • 1a Bräse S. Acc. Chem. Res. 2004; 37: 805
    • 1b Kimball DB, Haley MM. Angew. Chem. Int. Ed. 2002; 41: 3338
    • 1c Wang CM, Huang Y. Synlett 2013; 24: 145
    • 2a Wang CM, Sun H, Fang Y, Huang Y. Angew. Chem. Int. Ed. 2013; 52: 5795
    • 2b Wang CM, Chen H, Wang ZF, Chen JA, Huang Y. Angew. Chem. Int. Ed. 2012; 51: 7242
    • 2c Voica AF, Mendoza A, Gutekunst WR, Fraga JO, Baran PS. Nat. Chem. 2012; 4: 629
    • 2d Liu CY, Knochel P. J. Org. Chem. 2007; 72: 7106
    • 2e Liu CY, Knochel P. Org. Lett. 2005; 7: 2543
    • 2f Hejesen C, Petersen LK, Hansen NJ. V, Gothelf KV. Org. Biomol. Chem. 2013; 11: 2493
    • 2g Fang Y, Wang CM, Su SQ, Yu HZ, Huang Y. Org. Biomol. Chem. 2014; 12: 1061
    • 2h Hafner A, Bräse S. Adv. Synth. Catal. 2013; 355: 996
  • 3 Dobele M, Vanderheiden S, Jung N, Brase S. Angew. Chem. Int. Ed. 2010; 49: 5986
    • 4a Hafner A, Bräse S. Angew. Chem. Int. Ed. 2012; 51: 3713
    • 4b Hafner A, Bihlmeier A, Nieger M, Klopper W, Bräse S. J. Org. Chem. 2013; 78: 7938
    • 4c Hafner A, Feuerstein TJ, Bräse S. Org. Lett. 2013; 15: 3468
  • 5 Reingruber R, Vanderheiden S, Wagner A, Nieger M, Muller T, Es-Sayed M, Brase S. Eur. J. Org. Chem. 2008; 3314
  • 6 Tyrra W, Naumann D. J. Fluorine Chem. 2004; 125: 823