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Published on: August 12, 2019
Regioselective C-H Thiocyanation of Arenes by Iron(III) Chloride Catalysis
Lachlan J N Waddell1, Maisie R Senkans1, Andrew Sutherland1
1School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, U.K.
Abstract:
Aryl thiocyanates are flexible synthetic intermediates that can be used in the preparation of a diverse range of arene building blocks for medicinal chemistry. Here, we report a fast and efficient Lewis acid-catalyzed method for the regioselective thiocyanation of arenes. Iron(III) chloride was found to be an effective Lewis acid for the activation of N-thiocyanatosaccharin and the subsequent thiocyanation of a wide range of activated arenes. The procedure was applicable for the thiocyanation of biologically active compounds such as metaxalone and an estradiol derivative and was used as part of a one-pot tandem iron-catalytic process for the regioselective, dual functionalization of an arene building block.
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