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Regioselective Fluoroalkylarylation of Enamides Enabled by an Iron-Catalyzed Multicomponent Radical Cross-Coupling Strategy.

ABSTRACT: Fluoroalkylated compounds are important entities in agrochemicals, pharmaceuticals, and materials. The catalytic dicarbofunctionalization of alkenes represents a powerful strategy for the rapid construction and diversification of compounds. In this vein, multicomponent cross-coupling reactions (MC-CCR) can provide an efficient synthetic route to build molecular complexity. In this work, we report the first iron-catalyzed three-component fluoroalkylarylation of enamides via selective formation and trapping of α-amide radicals under mild conditions and fast reaction times. The reaction tolerates a variety of commercially available aryl Grignard reagents and fluoroalkyl halides. Finally, the use of a removable phthalimido group provides an efficient strategy to prepare highly valuable γ-difluoroalkylated amines.

SUBMITTER: Renteria-Gomez A

PROVIDER: S-EPMC10863403 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Regioselective Fluoroalkylarylation of Enamides Enabled by an Iron-Catalyzed Multicomponent Radical Cross-Coupling Strategy.

Rentería-Gómez Ángel Á Guerrero Macayla M Ramirez-Lopez Mireya M Gutierrez Osvaldo O

Organic letters 20230929 40

Fluoroalkylated compounds are important entities in agrochemicals, pharmaceuticals, and materials. The catalytic dicarbofunctionalization of alkenes represents a powerful strategy for the rapid construction and diversification of compounds. In this vein, multicomponent cross-coupling reactions (MC-CCR) can provide an efficient synthetic route to build molecular complexity. In this work, we report the first iron-catalyzed three-component fluoroalkylarylation of enamides via selective formation an ...[more]

PMID: 37773979

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