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A Bioinspired Organocatalytic Cascade for the Selective Oxidation of Amines under Air
Author(s) -
Largeron Martine,
Fleury MauriceBernard
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701402
Subject(s) - chemistry , imine , amine gas treating , pyrogallol , organocatalysis , catalysis , combinatorial chemistry , substrate (aquarium) , primary (astronomy) , monomer , cascade reaction , organic chemistry , enantioselective synthesis , polymer , oceanography , physics , astronomy , geology
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.