Synlett 2012; 23(11): 1621-1624
DOI: 10.1055/s-0031-1291163
letter
© Georg Thieme Verlag Stuttgart · New York

Direct C–H Arylation of Quinones with Anilines

Marc Lamblin*
a   Université de Bordeaux; CNRS UMR 5248, CBMN; IECB, 2 Rue Robert Escarpit, 33607 Pessac, France, Fax: +33(251)125402   Email: marclamblin@yahoo.fr
,
Guillaume Naturale
a   Université de Bordeaux; CNRS UMR 5248, CBMN; IECB, 2 Rue Robert Escarpit, 33607 Pessac, France, Fax: +33(251)125402   Email: marclamblin@yahoo.fr
,
Jean Dessolin
a   Université de Bordeaux; CNRS UMR 5248, CBMN; IECB, 2 Rue Robert Escarpit, 33607 Pessac, France, Fax: +33(251)125402   Email: marclamblin@yahoo.fr
,
François-Xavier Felpin*
b   Université de Nantes; CNRS UMR 6230, CEISAM; UFR des Sciences et des Techniques, 2 Rue de la Houssinière, 44322 Nantes Cedex 3, France, Email: fx.felpin@univ-nantes.fr
› Author Affiliations
Further Information

Publication History

Received: 26 March 2012

Accepted after revision: 19 April 2012

Publication Date:
13 June 2012 (online)


Abstract

We discovered that anilines were suitable for the direct C–H arylation of benzoquinone in the presence of tert-butyl nitrite. This new reaction proceeds through the in situ formation of a diazonium hydroxide species. The coupling can be carried out at room temperature under neutral, additive-free, metal-free, and aqueous conditions, allowing an environmentally friendly procedure.

Supporting Information

 
  • References

    • 1a Nikolovska-Coleska Z, Xu L, Hu Z, Tomita Y, Li P, Roller PP, Wang R, Fang X, Guo R, Zhang M, Lippman ME, Yang D, Wang S. J. Med. Chem. 2004; 47: 2430
    • 1b Viault G, Grée D, Das S, Yadav JS, Grée R. Eur. J. Org. Chem. 2011; 7: 1233
    • 2a Ushiyama K, Tanaka N, Ono H, Ogata H. J. Antibiot. 1971; 24: 197
    • 2b Fotso S, Maskey RP, Grün-Wollny I, Schulz K.-P, Munk M, Laatsch H. J. Antibiot. 2003; 56: 931
    • 2c Miller RF, Huang S. J Antibiot. 1995; 48: 520
    • 3a Koyama J. Recent Patents on Anti-Infective Drug Discovery 2006; 1: 113
    • 3b Shimizu S, Yamamoto Y, Koshimura S. Chem. Pharm. Bull. 1982; 30: 1896
    • 3c Kaji A, Saito R, Hata Y, Kiriyama N, Wakusawa S, Miyamoto K. Chem. Pharm. Bull. 1994; 42: 1682
  • 4 Zhang B, Salituro G, Szalkowski D, Li Z, Zhang Y, Royo I, Vitella D, Diez MT, Pelaez F, Ruby C, Kendall RL, Mao X, Griffin P, Calaycay J, Zierath JR, Heck JV, Smith RG, Moller DE. Science 1999; 284: 974
  • 5 Ortega A, Rincón Á, Jiménez-Aliaga KL, Bermejo-Bescós P, Martín-Aragón S, Molina MT, Csákÿ AG. Bioorg. Med. Chem. Lett. 2011; 21: 2183
    • 6a Gould SJ. Chem. Rev. 1997; 97: 2499
    • 6b Marco-Contelles J, Molina MT. Curr. Org. Chem. 2003; 7: 1433
    • 6c Kumamoto T, Ishikawa T, Omura S. Yuki Gosei Kagaku Kyokaishi 2004; 62: 49
  • 7 Coleman RS, Felpin F.-X, Chen W. J. Org. Chem. 2004; 69: 7309
  • 8 Abraham I, Joshi R, Pardasani P, Pardasani RT. J. Braz. Chem. Soc. 2011; 22: 385
    • 9a Best WM, Sims CG, Winslade M. Aust. J. Chem. 2001; 54: 401
    • 9b Lana EJ. L, Carazza F, De Oliveira RA. Helv. Chim. Acta 2004; 87: 1825
    • 9c Gan X, Jiang W, Wang W, Hu L. Org. Lett. 2009; 11: 589
    • 10a Itahara T. J. Org. Chem. 1985; 50: 5546
    • 10b Singh PK, Rohtagi BK, Khanna RN. Synth. Commun. 1992; 22: 987
    • 10c Zhao Y, Zhang Y, Wang J, Li H, Wu L, Liu Z. Synlett 2010; 2352
    • 10d Engler TA, Reddy JP. J. Org. Chem. 1991; 56: 6491
    • 10e Zhang H.-B, Liu L, Chen Y.-J, Wang D, Li C.-J. Adv. Synth. Catal. 2006; 348: 229
    • 10f Molina MT, Navarro C, Moreno A, Csákÿ AG. Org. Lett. 2009; 11: 4938
    • 10g Demchuk OG, Pietrusiewicz KM. Synlett 2009; 1149
    • 11a Fujiwara Y, Domingo V, Seiple IB, Gianatassio R, Del Bel M, Baran PS. J. Am. Chem. Soc. 2011; 133: 3292
    • 11b Seiple IB, Su S, Rodriguez RA, Gianatassio R, Fujiwara Y, Sobel AL, Baran PS. J. Am. Chem. Soc. 2010; 132: 13194
    • 11c Lockner JW, Dixon DD, Risgaard R, Baran PS. Org. Lett. 2011; 13: 5628
    • 12a Kochi JK, Bacha JD, Bethea TW. J. Am. Chem. Soc. 1967; 89: 6538
    • 12b Anderson JM, Kochi JK. J. Am. Chem. Soc. 1970; 92: 1651
    • 13a Minisci F, Vismara V, Fontana F, Morini G, Serravalle M, Giordano C. J. Org. Chem. 1986; 51: 4411
    • 13b Minisci F, Vismara E, Fontana F. Heterocycles 1989; 28: 489
    • 13c Minisci F, Fontana F, Vismara E. J. Heterocycl. Chem. 1990; 27: 79
  • 14 Commandeur C, Chalumeau C, Dessolin J, Laguerre M. Eur. J. Org. Chem. 2007; 3045
    • 15a Meerwein H, Büchner E, van Emster K. J. Prakt. Chem. 1939; 152: 237
    • 15b For a recent review of Meerwein arylation, see: Heinrich MR. Chem. Eur. J. 2009; 15: 820
    • 15c See also: Höfling S, Heinrich MR. Synthesis 2011; 173
  • 16 DeTar DF, Sagmanli S. J. Am. Chem. Soc. 1950; 72: 965
  • 17 Galli C. Chem. Rev. 1988; 88: 765
  • 18 Maroz A, Brede O. Radiat. Phys. Chem. 2003; 67: 275
  • 19 Bunnett JF, Takayama H. J. Am. Chem. Soc. 1968; 90: 5173