Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H

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Howard, Joseph L. ; Schotten, Christiane ; Alston, Stephen T. ; Browne, Duncan L. (2016)

We report an operationally simple, metal-free approach for the late-stage introduction of the important lipophilic hydrogen-bond donor motif, SCF2H. This reaction converts diaryl- and dialkyl-disulfides into the corresponding aryl/alkyl–SCF2H through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. This method is notable for its use of commercially available TMSCF2H, and does not rely on the need for handling of sensitive metal complexes.
  • References (16)
    16 references, page 1 of 2

    2 (a) B. E. Smart, J. Fluorine Chem., 2001, 109, 3; (b) M. Morgenthaler, E. Schweizer, A. Hoffmann-Ro¨der, F. Benini, R. E. Martin, G. Jaeschke, B. Wagner, H. Fischer, S. Bendels, D. Zimmerli, J. Schneider, F. Diederich, M. Kansy and K. Mu¨ller, ChemMedChem, 2007, 2, 1100; (c) R. Filler and R. Saha, Future Med. Chem., 2009, 1, 777; (d) D. B. Berkowitz and M. Bose, J. Fluorine Chem., 2001, 112, 13; (e) D. O'Hagan, J. Fluorine Chem., 2010, 131, 1071.

    3 (a) K. Mu¨ller, C. Faeh and F. Diederich, Science, 2007, 317, 1881; (b) M. Schlosser, Angew. Chem., Int. Ed., 1998, 110, 1496; (c) A. Bondi, J. Phys. Chem., 1964, 68, 441; (d) J. D. Dunitz and R. Taylor, Chem. - Eur. J., 1997, 3, 89.

    4 (a) B. D. Key, R. D. Howell and C. S. Criddle, Environ. Sci. Technol., 1997, 31, 2445; (b) D. O'Hagan, C. Schaffrath, S. L. Cobb, J. T. G. Hamilton and C. D. Murphy, Nature, 2002, 416, 279; (c) G. W. Gribble, Naturally Occurring Organofluorines, in Handbook of Environmental Chemistry, ed. A. H. Neilson, Springer-Verlag, Berlin, vol. 3, part N, 2002.

    5 (a) X. Chen, S. Hussain, S. Parveen, S. Zhang, Y. Yang and C. Zhu, Curr. Med. Chem., 2012, 19, 3578; (b) R. Bentley, Chem. Soc. Rev., 2005, 34, 609.

    6 (a) V. N. Boiko, Beilstein J. Org. Chem., 2010, 6, 880; (b) J. F. Giudicelli, C. Richer and A. Berdeaux, Br. J. Clin. Pharmacol., 1976, 3, 113; (c) M. Diaferia, F. Veronesi, G. Morganti, L. Nisoli and D. P. Fioretti, Parasitol. Res., 2013, 112, 163.

    7 C. Hansch, A. Leo, S. H. Unger, K. H. Kim, D. Nikaitani and E. J. Lien, J. Med. Chem., 1973, 16, 1207.

    8 (a) J. Hine and J. J. Porter, J. Am. Chem. Soc., 1960, 82, 6118; (b) P. Deprez and J. P. Vevert, J. Fluorine Chem., 1996, 80, 159; (c) Y. Zafrani, G. Sod-Moriah and Y. Segall, Tetrahedron, 2009, 65, 5278; (d) K. Fuchibe, M. Bando, R. Takayama and J. Ichikawa, J. Fluorine Chem., 2015, 171, 133; (e) V. P. Mehta and M. F. Greaney, Org. Lett., 2013, 15, 5036; ( f ) G. K. Surya Prakash, S. Krishnamoorthy, S. Kar and G. A. Olah, J. Fluorine Chem., 2015, 180, 186; (g) W. Zhang, J.-M. Zhu and J.-B. Hu, Tetrahedron Lett., 2008, 49, 5006; (h) Y. Fujiwara, J. A. Dixon, R. A. Rodriguez, R. D. Baxter, D. D. Dixon, M. R. Collin, D. G. Blackmond and P. S. Baran, J. Am. Chem. Soc., 2012, 134, 1494; (i) W. Zhang, F. Wang and J. Hu, Org. Lett., 2009, 11, 2109; ( j) G. K. Surya Prakash, Z. Zhang, F. Wang, C.-F. Ni and G. A. Olah, J. Fluorine Chem., 2011, 132, 792; (k) L.-C. Li, F. Wang, C.-F. Ni and J.-B. Hu, Angew. Chem., Int. Ed., 2013, 52, 12390.

    9 D. Zhu, Y. Gu, L. Lu and Q. Shen, J. Am. Chem. Soc., 2015, 137, 10547.

    10 J. Wu, Y. Gu, X. Leng and Q. Shen, Angew. Chem., Int. Ed., 2015, 54, 7648.

    11 (a) B. Bayarmagnai, C. Matheis, K. Jouvin and L. J. Gooßen, Angew. Chem., Int. Ed., 2015, 54, 5753; (b) K. Jouvin, C. Matheis and L. J. Gooßen, Chem. - Eur. J., 2015, 21, 14324; (c) C. Matheis, M. Wang, T. Krause and L. J. Gooßen, Synlett, 2015, 1628; (d) G. Danoun, B. Bayarmagnai, M. F. Gruenberg and L. J. Gooßen, Chem. Sci., 2014, 5, 1312.

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