Unknown

Dataset Information

0

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

altmetric image

Publications

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]

Similar Datasets

| S-EPMC7641471 | biostudies-literature
| S-EPMC8162457 | biostudies-literature
| S-EPMC8718116 | biostudies-literature
| S-EPMC5909123 | biostudies-literature
| S-EPMC6482061 | biostudies-literature
| S-EPMC6178801 | biostudies-literature
| S-EPMC6405340 | biostudies-literature
| S-EPMC8956603 | biostudies-literature
| S-EPMC8629995 | biostudies-literature
| S-EPMC7014401 | biostudies-literature