Synthesis 2015; 47(13): 1937-1943
DOI: 10.1055/s-0034-1380517
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isatins through Direct Oxidation of Indoles with IBX-SO3K/NaI

Angla Bredenkamp
a   Organic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
,
Fabian Mohr
b   Inorganic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany
,
Stefan F. Kirsch*
a   Organic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
› Author Affiliations
Further Information

Publication History

Received: 23 February 2015

Accepted: 09 March 2015

Publication Date:
21 April 2015 (online)


Abstract

The direct conversion of indoles into isatins is presented. The reagent mixture NaI/IBX-SO3K, containing a sulfonylated derivative of 2-iodoxybenzoic acid, was employed to trigger this oxidative process. Moreover, the synthetic route toward IBX-SO3K and the X-ray crystal structure of the title compound are described in great detail.

Supporting Information

 
  • References


    • For recent reviews, see:
    • 1a Yusubov MS, Zhdankin VV. Curr. Org. Synth. 2012; 9: 247
    • 1b Zhdankin VV. J. Org. Chem. 2011; 76: 1185
    • 1c Quideau S, Wirth T. Tetrahedron 2010; 66: 5737
    • 1d Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
    • 2a Hartmann C, Meyer V. Ber. Dtsch. Chem. Ges. 1893; 26: 1727
    • 2b Satam V, Harad A, Rajule R, Pati H. Tetrahedron 2010; 66: 7659
    • 2c Duschek A, Kirsch SF. Angew. Chem. Int. Ed. 2011; 50: 1524
    • 3a Frigerio M, Santagostino M, Sputore S. J. Org. Chem. 1999; 64: 4537
    • 3b Frigerio M, Santagostino M. Tetrahedron Lett. 1994; 35: 8019
    • 3c More JD, Finney NS. Org. Lett. 2002; 4: 3001
    • 3d Bartlett SL, Beaudry CM. J. Org. Chem. 2011; 76: 9852
    • 4a Boppisetti JK, Birman VB. Org. Lett. 2009; 11: 1221
    • 4b Gagnepain J, Castet F, Quideau S. Angew. Chem. Int. Ed. 2007; 46: 1533
    • 4c Magdziak D, Rodriguez AA, Van De Water RW, Pettus TR. R. Org. Lett. 2002; 4: 285
    • 5a Nicolaou KC, Montagnon T, Baran PS, Zhong Y.-L. J. Am. Chem. Soc. 2002; 124: 2245
    • 5b Nicolaou KC, Montagnon T, Baran PS. Angew. Chem. Int. Ed. 2002; 41: 993
    • 5c Klahn P, Kirsch SF. Eur. J. Org. Chem. 2014; 15: 3149
    • 6a Nicolaou KC, Mathison CJ, Montagnon T. J. Am. Chem. Soc. 2004; 126: 5192
    • 6b Nicolaou KC, Zhong Y.-L, Baran PS, Barluenga S, Hunt KW, Kranich R. J. Am. Chem. Soc. 2002; 124: 2233
    • 7a Kirsch SF. J. Org. Chem. 2005; 70: 10210
    • 7b Binder JT, Crone B, Kirsch SF, Liébert C, Menz H. Eur. J. Org. Chem. 2007; 1636
    • 7c Crone B, Kirsch SF. Chem. Commun. 2006; 764
    • 7d Duschek A, Kirsch SF. Chem. Eur. J. 2009; 15: 10713
  • 8 Umland K.-D, Mayer C, Kirsch SF. Synlett 2014; 25: 813
    • 9a Harschneck T, Hummel S, Kirsch SF, Klahn P. Chem. Eur. J. 2012; 18: 1187
    • 9b Klahn P, Erhardt H, Kotthaus A, Kirsch SF. Angew. Chem. Int. Ed. 2014; 53: 7913
    • 10a Mülbaier M, Giannis A. Angew. Chem. Int. Ed. 2001; 40: 4393
    • 10b Sorg G, Mengel A, Jung G, Rademann J. Angew. Chem. Int. Ed. 2001; 40: 4395
    • 11a Katritzky AR, Duell BL, Durst HD, Knier BL. J. Org. Chem. 1988; 53: 3972
    • 11b Richardson RD, Zayed JM, Altermann S, Smith D, Wirth T. Angew. Chem. Int. Ed. 2007; 46: 6529
    • 11c Moorthy JN, Singhal N, Senapati K. Tetrahedron Lett. 2008; 49: 80
    • 11d Kommreddy A, Bowsher MS, Gunna MR, Botha K, Vinod TK. Tetrahedron Lett. 2008; 49: 4378
    • 11e Narsimha Moorthy JN, Senapati K, Parida KN, Jhulki S, Sooraj K, Nair NN. J. Org. Chem. 2011; 76: 9593
  • 12 Thottumkara AP, Vinod TK. Tetrahedron Lett. 2002; 43: 569
  • 13 Cui L.-Q, Dong Z.-L, Liu K, Zhang C. Org. Lett. 2011; 13: 6488
    • 14a Zhdankin VV, Litvinov DN, Koposov AY, Ferguson MJ, McDonald R, Tykwinski RR. Chem. Commun. 2004; 106
    • 14b Zhdankin VV, Koposov AY, Litvinov DN, Ferguson MJ, McDonald R, Luu T, Tykwinski RR. J. Org. Chem. 2005; 70: 6484
  • 15 Zhdankin VV, Koposov AY, Netzel BC, Yashin NV, Rempel BP, Ferguson MJ, Tykwinski RR. Angew. Chem. Int. Ed. 2003; 42: 2194
  • 16 Koposov AY, Litvinov DN, Zhdankin VV. Tetrahedron Lett. 2004; 45: 2719
    • 17a Yoshimura A, Banek CT, Yusubov MS, Nemykin VN, Zhdankin VV. J. Org. Chem. 2011; 76: 3812
    • 17b Moorthy JN, Senapati K, Parida KN. J. Org. Chem. 2010; 75: 8416
    • 17c Mailyan AK, Geraskin IM, Nemykin VN, Zhdankin VV. J. Org. Chem. 2009; 74: 8444

      Related oxidative functionalizations:
    • 18a Moorthy JN, Senapati K, Kumar S. J. Org. Chem. 2009; 74: 6287
    • 18b Dolenc D. Synthesis 2000; 544
    • 19a Chen S, Liu Z, Shi E, Chen L, Wei W, Li H, Cheng Y, Wan X. Org. Lett. 2011; 13: 2274
    • 19b Liu XL, Chen WZ. Organometallics 2012; 31: 6614
  • 20 Sriram R, Kumar CN. S. S. P, Raghunandan N, Ramesh V, Sarangapani M, Rao VJ. Synth. Commun. 2012; 42: 3419
  • 21 Kumar CN. S. S. P, Devi CL, Rao VJ, Palaniappan S. Synlett 2008; 2023
  • 22 Zi Y, Cai ZJ, Wang S.-Y, Ji S.-J. Org. Lett. 2014; 16: 3094
    • 23a Yadav JS, Reddy BV. S, Reddy CS, Krishna AD. Synthesis 2007; 693
    • 23b Yadav JS, Reddy BV. S, Reddy CS, Krishna AD. Tetrahedron Lett. 2007; 48: 2029
  • 24 Zhou D, Chu W, Chen DL, Wang Q, Reichert DE, Rothfuss J, D’Avignon A, Welch MJ, Mach RH. Org. Biomol. Chem. 2009; 7: 1337
    • 25a Stevenson PJ, Treacy AB, Nieuwenhuyzen M. J. Chem. Soc., Perkin Trans. 2 1997; 589
    • 25b Gougoutas JZ. Cryst. Struct. Commun. 1981; 10: 489
  • 26 McAllister LA, McCormick RA, James KM, Brand S, Willetts N, Procter DJ. Chem. Eur. J. 2007; 13: 1032
  • 27 Morales-Rios MS, Joseph-Nathan P. Magn. Reson. Chem. 1991; 29: 893
  • 28 Tang B.-X, Song R.-J, Wu C.-Y, Liu Y, Zhou M.-B, Wie W.-T, Deng G.-B, Yin D.-L, Li J.-H. J. Am. Chem. Soc. 2010; 132: 8900
  • 29 CCDC-1050515 contains the supplementary crystallographic data for 6f. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; E-mail: deposit@ccdc.cam.ac.uk.
  • 30 Sin N, Venables BL, Liu X, Huang S, Gao Q, Ng A, Dalterio R, Rajamani R, Meanwell NA. J. Heterocycl. Chem. 2009; 46: 432
  • 31 CCDC 1050503 contains the supplementary crystallographic data for 2. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge­ Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.