Visible‐Light‐Induced Photoreduction of Carborane Phosphonium Salts: Efficient Synthesis of Carborane‐Oxindole‐Pharmaceutical Hybrids

Abstract

AbstractVisible‐light‐induced photoreaction of carboranes is an effective approach to prepare carborane‐containing compounds. While several methods involving boron‐centered carboranyl radicals have been established, those for carbon‐centered carboranyl radicals are underdeveloped, except for the UV‐light‐promoted photohomolysis. Herein, we describe a simple but effective approach to access carbon‐centered carboranyl radicals by photoreduction of carborane phosphonium salts under blue light irradiation without using transition metals and photocatalysts. The utility of the method was demonstrated by successfully preparing a range of carborane‐oxindole‐pharmaceutical hybrids by radical cascade reactions. Computational and experimental studies suggest that the carbon‐centered carboranyl radicals are generated by single‐electron transfer of the photoactive charge‐transfer complexes between the salts and the additive potassium acetate.