Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 14, Pages 4241-4245Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201412256
Keywords
aldehydes; cyanides; oxidation; reaction mechanisms; synthetic methods
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Funding
- National Science Foundation [CHE-0847262]
- University of Connecticut Office of Undergraduate Research
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0847262] Funding Source: National Science Foundation
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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.
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