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 2005(6): 961-964
DOI: 10.1055/s-2005-861852
DOI: 10.1055/s-2005-861852
PAPER
© Georg Thieme Verlag Stuttgart · New York
Ferric(III) Chloride-Promoted Electrophilic Thiocyanation of Aromatic and Heteroaromatic Compounds [1]
Further Information
Received
26 August 2004
Publication Date:
09 March 2005 (online)
Publication History
Publication Date:
09 March 2005 (online)
Abstract
Indoles, oxindoles and aromatic amino compounds undergo smooth thiocyanation with ammonium thiocyanate in the presence of anhydrous FeCl3 in dichloromethane under mild conditions to afford the corresponding 3-indolyl and 4-aryl thiocyanates, respectively, in high yields with excellent selectivity. The use of ferric chloride makes it quite simple, more convenient and practical. This new method offers several advantages such as high conversions, cleaner reaction profiles, short reaction times, and the use of inexpensive and readily available catalyst.
Key words
thiocyanation - electrophilic substitution - aromatic systems - aryl thiocyanates
IICT Communication No: 041214.
-
2a
Wood JL. Org. React. 1946, 3: 240 -
2b
Kelly TR.Kim MH.Curtis ADM. J. Org. Chem. 1993, 58: 5855 - 3
Guy RG. In The Chemistry of Cyanates and Their Thio Derivatives Part 2:Patai S. Wiley; New York: 1977. Chap. 18. p.819 -
4a
Toste FD.Laronde F.Still WJ. Tetrahedron Lett. 1995, 36: 2949 -
4b
Grant MS.Snyder HR. J. Am. Chem. Soc. 1960, 82: 2742 -
5a
Kita Y.Takeda T.Mihara S.Whelan BA.Thoma H. J. Org. Chem. 1995, 60: 7144 -
5b
Yadav JS.Reddy BVS.Shubashree S.Sadashiv K. Tetrahedron Lett. 2004, 45: 2951 -
6a
Toste FD.De Stefano V.Still WJ. Synth. Commun. 1995, 25: 1277 -
6b
Nair V.George TG.Nair LG.Panicker SB. Tetrahedron Lett. 1999, 40: 1195 - 7
Chakrabarty M.Sarkar S. Tetrahedron Lett. 2003, 44: 8131 -
8a
Christoffers J. J. Chem. Soc., Perkin Trans. 1 1997, 3141 -
8b
Christoffers J.Oertling H. Tetrahedron 2000, 56: 1339 -
8c
Lu J.Ma H. Synlett 2000, 63 -
8d
Masson C.Soto J.Bessodes M. Synlett 2000, 1281 -
8e
Chibiryaev AM.Kimpe ND.Tkachev AV. Tetrahedron Lett. 2000, 41: 8011
References
IICT Communication No: 041214.