Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 36, Pages 11227-11231Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b08145
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Funding
- NIH [R01 GM100143, 1S10 OD020022-1]
- AbbVie
- NSF [CHE-1048642]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM100143] Funding Source: NIH RePORTER
- OFFICE OF THE DIRECTOR, NATIONAL INSTITUTES OF HEALTH [S10OD020022] Funding Source: NIH RePORTER
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Secondary piperidines are ideal pharmaceutical building blocks owing to the prevalence of piperidines in commercial drugs. Here, we report an electrochemical method for cyanation of the heterocycle adjacent to nitrogen without requiring protection or substitution of the N-H bond. The reaction utilizes ABNO (9-azabicyclononane N-oxyl) as a catalytic mediator. Electrochemical oxidation of ABNO generates the corresponding oxoammonium species, which promotes dehydrogenation of the 2 piperidine to the cyclic imine, followed by addition of cyanide. The low-potential, mediated electrolysis process is compatible with a wide range of heterocyclic and oxidatively sensitive substituents on the piperidine ring and enables synthesis of unnatural amino acids.
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