Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis.
Methods for the direct C-H functionalization of aromatic compounds are in demand for a variety of applications, including the synthesis of agrochemicals, pharmaceuticals, and materials. Herein, we disclose the construction of aromatic nitriles via direct C-H functionalization using an acridinium photoredox catalyst and trimethylsilyl cyanide under an aerobic atmosphere. The reaction proceeds at room temperature under mild conditions and has proven to be compatible with a variety of electron-donating and -withdrawing groups, halogens, and nitrogen- and oxygen-containing heterocycles, as well as aromatic-containing pharmaceutical agents.
Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
Joshua B
JB
McManus
Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
David A
0000-0003-1199-9879
DA
Nicewicz
D000166:Acridines / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013696:Temperature
D000166:Acridines; D009570:Nitriles; D047250:Calixarenes