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 ofN-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.