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An ?-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung.

ABSTRACT: The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into ?-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.

SUBMITTER: Bauer A 

PROVIDER: S-EPMC7589340 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung.

Bauer Adriano A   Di Mauro Giovanni G   Li Jing J   Maulide Nuno N  

Angewandte Chemie (International ed. in English) 20200817 41

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations. ...[more]

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