Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 28, Pages 6763-6767Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201701402
Keywords
biomimetics; cross-coupling; imines; organocatalysis; primary amines
Categories
Funding
- CNRS
- Paris Descartes University
Ask authors/readers for more resources
A bioinspired organocatalytic cascade reaction for the selective aerobic oxidative cross-coupling of primary amines to imines is described. This approach takes advantages of commercially available pyrogallol monomeric precursor to deliver low loadings of natural purpurogallin in situ, under air. This is further engaged in a catalytic process with the amine substrate affording, under single turnover, the active biomimetic quinonoid organocatalyst and the homocoupled imine intermediate, which is then converted into cross-coupled imine after dynamic transimination. This organocatalytic cascade inspired by both purpurogallin biosynthesis and copper amine oxidases allows the aerobic oxidation of non-activated primary amines that non-enzymatic organocatalysts were not able to accomplish alone.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available