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Synthesis 2008(23): 3779-3782  
DOI: 10.1055/s-0028-1083636
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

IBX: A Novel and Versatile Oxidant for Electrophilic Thiocyanation of Indoles, Pyrrole and Arylamines

Jhillu S. Yadav*, Basi V. Subba Reddy, B. Bala Murali Krishna
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: 0091 40 27160512; e-Mail: yadav@iict.res.in;
Further Information

Publication History

Received 17 June 2008
Publication Date:
06 November 2008 (online)

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Abstract

The direct thiocyanation of indoles and pyrrole with ammonium thiocyanate has been achieved using o-iodoxybenzoic acid (IBX) under mild and neutral conditions to produce indol-3-yl and pyrrol-2-yl thiocyanates, respectively, in excellent yields and with high selectivity. This method is effective even with N-substituted arylamines for the preparation of aryl thiocyanates.

Key words

o-iodoxybenzoic acid - electrophilic substitution - indoles - aryl thiocyanates - heteroaryl thiocyanates

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