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Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination.

ABSTRACT: A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important γ-lactones in one further step.

SUBMITTER: Basnet P

PROVIDER: S-EPMC7885264 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination.

Basnet Prakash P Hong Gang G Hendrick Charles E CE Kozlowski Marisa C MC

Organic letters 20210104 2

A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important γ-lactones in one further step. ...[more]

PMID: 33393785

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