ol7b03620_si_001.pdf (4.75 MB)
Aerobic, Diselenide-Catalyzed Redox Dehydration: Amides and Peptides
journal contributionposted on 2018-01-11, 19:50 authored by Srirama Murthy Akondi, Pavankumar Gangireddy, Thomas C. Pickel, Lanny S. Liebeskind
At 2.5 mol % loadings using reaction temperatures between 30–55 °C, ortho-functionalized diaryl diselenides are highly effective organocatalytic oxidants for aerobic redox dehydrative amidic and peptidic bond formation using triethyl phosphite as a simple terminal reductant. This simple-to-perform organocatalytic reaction relies on the ability of selenols to react directly with dioxygen in air without recourse to metal catalysts. It represents an important step toward the development of a general, economical, and benign catalytic redox dehydration protocol.
terminal reductantAerobicmoldioxygenselenol2.5loadingPeptideredox dehydrative amidicDiselenide-Catalyzed Redox Dehydrationreaction temperaturesorganocatalytic oxidantsabilityAmideredox dehydration protocolmetal catalystsrecoursesimple-to-perform organocatalytic reactionpeptidic bond formationtriethyl phosphiteortho-functionalized diaryl diselenides