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Electrochemical Functional-Group-Tolerant Shono-type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators.

ABSTRACT: An electrochemical method has been developed for ?-oxygenations of cyclic carbamates by using a bicyclic aminoxyl as a mediator and water as the nucleophile. The mediated electrochemical process enables substrate oxygenation to proceed at a potential that is approximately 1?V lower than the redox potential of the carbamate substrate. This feature allows for functional-group compatibility that is inaccessible with conventional Shono oxidations, which proceed by direct electrochemical substrate oxidation. This reaction also represents the first ?-functionalization of non-activated cyclic carbamates with oxoammonium oxidants.

SUBMITTER: Wang F

PROVIDER: S-EPMC6201259 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Electrochemical Functional-Group-Tolerant Shono-type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators.

Wang Fei F Rafiee Mohammad M Stahl Shannon S SS

Angewandte Chemie (International ed. in English) 20180502 22

An electrochemical method has been developed for α-oxygenations of cyclic carbamates by using a bicyclic aminoxyl as a mediator and water as the nucleophile. The mediated electrochemical process enables substrate oxygenation to proceed at a potential that is approximately 1 V lower than the redox potential of the carbamate substrate. This feature allows for functional-group compatibility that is inaccessible with conventional Shono oxidations, which proceed by direct electrochemical substrate ox ...[more]

PMID: 29659129

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