Heteroarenes and arenes that contain
electron-withdrawing groups
are chlorinated in good to excellent yields (scalable to gram scale)
using trichloroisocyanuric acid (TCCA) and catalytic Brilliant
Green (BG). Visible-light activation of BG serves to amplify the electrophilic
nature of TCCA, providing a mild alternative approach to acid-promoted
chlorination of deactivated (hetero)aromatic substrates. The utility
of the TCCA/BG system is demonstrated through comparison to other
chlorinating reagents and by the chlorination of pharmaceuticals including
caffeine, lidocaine, and phenazone.
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