Synthesis 2022(6): 961-964  
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]

J. S. Yadav*, B. V. S. Reddy, A. D. Krishna, Ch. Suresh Reddy, A. V. Narsaiah
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: 91(40)27160512; e-Mail: yadavpub@iict.res.in;
Further Information

Publication History

Received 26 August 2004
Publication Date:
09 March 2005 (online)

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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

1

IICT Communication No: 041214.

1

IICT Communication No: 041214.