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Synthesis 2004(12): 1983-1986  
DOI: 10.1055/s-2004-829150
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© Georg Thieme Verlag Stuttgart · New York

Ferric(III) Chloride-Promoted Efficient Thiocyanation of Arylalkenes: A Facile Synthesis of Dithiocyanates

J. S. Yadav*, B. V. S. Reddy, Manoj Kumar Gupta
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 15 March 2004
Publication Date:
13 July 2004 (online)

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Abstract

Anhydrous FeCl3 oxidizes potassium thiocyanate to the corresponding radical and promotes subsequent addition to nucleophilic olefins to produce dithiocyanate derivatives under mild conditions with high efficiency. Excellent yields and chemoselectivities together with the environmental-friendly nature of the Fe(III) chloride makes this method an attractive alternative to established methods. 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

oxidative radical addition - alkenes - dithiocyanates