title: Access to nitriles from aldehydes mediated by an oxoammonium salt.
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.
authors: Department of Chemistry, University of Connecticut, 55 N. Eagleville Road, Storrs, CT 06269-3060 (USA).
authors: Christopher B
authors: CB
authors: Kelly
authors: Kyle M
authors: KM
authors: Lambert
authors: Michael A
authors: MA
authors: Mercadante
authors: John M
authors: JM
authors: Ovian
authors: William F
authors: WF
authors: Bailey
authors: Nicholas E
authors: NE
authors: Leadbeater
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D064751:Ammonium Compounds / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D012492:Salts / Q000737:chemistry
chemical_list: D000447:Aldehydes; D064751:Ammonium Compounds; D009570:Nitriles; D012492:Salts
keywords: aldehydes; cyanides; oxidation; reaction mechanisms; synthetic methods