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Three-component ruthenium-catalyzed remote C-H functionalization of 8-aminoquinoline amides.

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Multicomponent reactions can efficiently construct complex molecular structures from simple precursors. Herein, a novel ruthenium-catalyzed three-component highly selective remote C-H functionalization of 8-aminoquinoline amides has been described. The reaction tolerates… Click to show full abstract

Multicomponent reactions can efficiently construct complex molecular structures from simple precursors. Herein, a novel ruthenium-catalyzed three-component highly selective remote C-H functionalization of 8-aminoquinoline amides has been described. The reaction tolerates a wide range of functional groups, producing arylation/difluoroalkylation products of olefins with potential biological activity and pharmaceutical value. Radical scavenging and radical clock experiments show that a free radical process is involved and a H/D exchange experiment suggests that the reaction might involve ortho-C-H activation of the aromatic ring. A possible mechanism is proposed.

Keywords: functionalization aminoquinoline; remote functionalization; aminoquinoline amides; three component; ruthenium catalyzed

Journal Title: Chemical communications
Year Published: 2020

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