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Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation.

ABSTRACT: Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors.

SUBMITTER: Sweeney JB

PROVIDER: S-EPMC6240703 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation.

Sweeney Joseph B JB Doulcet Julien J Thapa Bimod B

iScience 20181101

Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with ...[more]

PMID: 30448732

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