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- Title
Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt.
- Authors
Kelly, Christopher B.; Lambert, Kyle M.; Mercadante, Michael A.; Ovian, John M.; Bailey, William F.; Leadbeater, Nicholas E.
- Abstract
A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.
- Subjects
NITRILES; ALDEHYDES; CHEMICAL yield; OXIDATION; IMINES; CHEMICAL amplification
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 14, p4315
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201412256