Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2022(9): 1520-1524
DOI: 10.1055/s-0028-1088035
DOI: 10.1055/s-0028-1088035
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Iron(III) Chloride: A Versatile Catalyst for the Practical Synthesis of 3-Sulfenylindoles
Further Information
Received
15 December 2008
Publication Date:
25 March 2009 (online)
Publication History
Publication Date:
25 March 2009 (online)
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
-
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 -
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