Chemoselective α,β-Dehydrogenation of Saturated Amides.

ABSTRACT: We report a method for the selective α,β-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium-mediated dehydrogenation. The α,β-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic Se^IV species.

SUBMITTER: Teskey CJ 

PROVIDER: S-EPMC6348382 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature