1,2-Acylcyanation of Styrenes by Photoinduced Nickel Catalysis to Generate Acyl Radicals from Acyl Fluorides

We report herein a photoinduced nickel-catalyzed 1,2-acylcyanation of styrenes with acyl fluorides and trimethylsilyl cyanide (TMSCN). Nickel(II) acyl complexes, formed from nickel(0) complexes and acyl fluorides, are photoexcited to generate acyl radicals via a ligand-to-metal charge transfer (LMCT) process. This transformation proceeds under mild conditions and thus can be applied to the late-stage functionalization (LSF) of natural product derivatives. Synthetic derivatizations show the utility of the products. The preparation of aza-DIPYs is also demonstrated.