Premium
Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt
Author(s) -
Kelly Christopher B.,
Lambert Kyle M.,
Mercadante Michael A.,
Ovian John M.,
Bailey William F.,
Leadbeater Nicholas E.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201412256
Subject(s) - salt (chemistry) , nitrile , aldehyde , tetrafluoroborate , chemistry , imine , silylation , ammonia , combinatorial chemistry , organic chemistry , polymer chemistry , catalysis , ionic liquid
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.