Site-Selective Ruthenium-Catalyzed C–H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2019

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

Résumé

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.

Domaines

Chimie
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Dates et versions

hal-02322072 , version 1 (21-10-2019)

Identifiants

Citer

Yu-Chao Yuan, Christian Bruneau, Thierry Roisnel, Rafael Gramage-Doria. Site-Selective Ruthenium-Catalyzed C–H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group. Journal of Organic Chemistry, 2019, 84 (20), pp.12893-12903. ⟨10.1021/acs.joc.9b01563⟩. ⟨hal-02322072⟩
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