Site-Selective Ruthenium-Catalyzed C–H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group

Biologically relevant N-arylisoindolinones efficiently
underwent arylation reactions under ruthenium catalysis via C–H
bond functionalization. The reactions exclusively led to monoarylated
products, and only ortho selectivity was observed
in the aromatic ring connected to the nitrogen atom. Interestingly,
no C–H bond functionalization was observed in the other benzene
ring in the ortho position with respect to the carbonyl
group. This ruthenium-catalyzed reaction displayed a high functional
group tolerance, and it employed readily available and benchmark stable
boronic acid and potassium aryltrifluoroborate derivatives as coupling
partners. An appealing late-stage functionalization of indoprofen
applying this methodology is showcased.