The generation and control of aryl radicals pose considerable challenges, such as highly negative reduction potentials of aryl halides and their amphiphilic character. Herein, we introduce the synergistic interplay of three-component photoactive electron-transfer system that enables photoinduced cross-coupling of aryl halides using n-tetrabutylphosphonium phthalate as a one-electron-transfer mediator. Our method readily accommodates the formation of four different bonding-forming reaction (C(sp2)–C/P/B/S). The present approach exhibits good functional group tolerance, biocompatibility with plasmid, DNase and serum albumin as well as great efficiency for late-stage incorporation into drug molecules, BODIPY dye and natural compounds. Mechanistic investigations revealed the bifunctional property of n-tetrabutylphosphonium phthalate potentially through two-point non-covalent interaction to bring aryl halides and pyrrole derivatives within proximity to facilitate electron transfer.

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