Iron(III) Chloride: A Versatile
Catalyst for the Practical Synthesis of 3-Sulfenylindoles

Jhillu S. Yadav; Basi V. Subba Reddy; Yerabolu Jayasudhan Reddy; Karanam Praneeth

doi:10.1055/s-0028-1088035

PAPER

Iron(III) Chloride: A Versatile Catalyst for the Practical Synthesis of 3-Sulfenylindoles

Jhillu S. Yadav*, Basi V. Subba Reddy, Yerabolu Jayasudhan Reddy, Karanam Praneeth
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;

Abstract

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Abstract

The direct sulfenylation of indoles with aromatic thiols has been accomplished in the presence of 20 mol% of FeCl₃ in refluxing acetonitrile to produce 3-arylthioindoles in relatively good to excellent yields and with high selectivity. This method works even with 2-unsubstituted indoles.

Key words

thiolation - indoles - thiols - 3-arylthioindoles

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References

1a Avis I. Martinez A. Tauler J. Zudaire E. Mayburd A. Abu-Ghazaleh R. Ondrey F. Mulshine JL. Cancer Res. 2005, 65: 4181

1b De Martino G. La Regina G. Coluccia A. Edler MC. Barbera MC. Brancale A. Wilcox E. Hamel E. Artico M. Silvestri R. J. Med. Chem. 2004, 47: 6120

1c Funk CD. Nat. Rev. Drug Discov. 2005, 4: 664

1d Khandekar SS. Gentry DR. Van Aller GS. Doyle ML. Chambers PA. Konstantinidis AK. Brandt M. Daines RA. Lonsdale JT. J. Biol. Chem. 2001, 276: 30024

2a Williams TM. Ciccarone TM. MacTough SC. Rooney CS. Balani SK. Condra JH. Emini EA. Goldman ME. Greenlee WJ. Kauffman LR. O’Brien JA. Sardana VV. Schleif WA. Theoharides AD. Anderson PS. J. Med. Chem. 1993, 36: 1291

2b Silvestri R. De Martino G. La Regina G. Artico M. Massa S. Vargiu L. Mura M. Loi AG. Marceddu T. La Colla P. J. Med. Chem. 2003, 46: 2482

2c Hamel P. J. Org. Chem. 2002, 67: 2854

3a Ranken PF. McKinnie BG. J. Org. Chem. 1989, 54: 2985

3b Maeda Y. Koyabu M. Nishimura T. Uemura S. J. Org. Chem. 2004, 69: 7688

4a Atkinson JG. Hamel P. Girard Y. Synthesis 1988, 480

4b Scoffone E. Fontana A. Rocchi R. Biochemistry 1968, 7: 971

4c Anzai K. J. Heterocycl. Chem. 1979, 16: 567

5a Raban M. Chern L. J. Org. Chem. 1980, 45: 1688

5b Ranken PF. McKinnie BG. J. Org. Chem. 1989, 54: 2985

5c Browder CC. Mitchell MO. Smith RL.
El-Sulayman G. Tetrahedron Lett. 1993, 34: 6245

6a Matsugi M. Murata K. Gotanda K. Nambu H. Anilkumar G. Matsumoto K. Kita Y. J. Org. Chem. 2001, 66: 2434

6b Tudge M. Tamiya M. Savarin C. Humphrey GR. Org. Lett. 2006, 8: 565

6c Horiguchi Y. Sonobe A. Saitoh K. Toda J. Sano T. Chem. Pharm. Bull. ,

7 Schlosser KM. Krasutsky AP. Hamilton HW. Reed JE. Sexton K. Org. Lett. 2004, 6: 819

8a Maeda Y. Koyabu M. Nishimura T. Uemura S. J. Org. Chem. 2004, 69: 7688

8b Campbell JA. Broka CA. Gong L. Walker KAM. Wang J.-H. Tetrahedron Lett. 2004, 45: 4073

9a Bolm C. Legros J. Paiti JL. Zani L. Chem. Rev. 2004, 104: 6217

9b Ruping M. Nactshim BJ. Scheidt T. Org. Lett. 2006, 8: 3717

9c Komeyma K. Morimoto T. Takaki K. Angew. Chem. Int. Ed. 2006, 45: 2938

9d Kischel J. Jovel I. Mertins K. Zapf A. Beller M. Org. Lett. 2006, 8: 19

9e Diaz DD. Miranda PO. Padron JI. Martin VS. Curr. Org. Chem. 2006, 10: 457

9f Iovel I. Kristin M. Kischel J. Zapf A. Mathias B. Angew. Chem. Int. Ed. 2005, 44: 3913