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Amine Functionalization through Sequential Quinone‐Catalyzed Oxidation/Nucleophilic Addition
Author(s) -
Leon Martin A.,
Liu Xinyun,
Phan Johnny H.,
Clift Michael D.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600786
Subject(s) - chemistry , nucleophile , surface modification , quinone , amine gas treating , catalysis , combinatorial chemistry , organocatalysis , nucleophilic addition , organic chemistry , photoredox catalysis , oxidative phosphorylation , enantioselective synthesis , photocatalysis , biochemistry
A simple and efficient method for the synthesis of α‐branched amines through formal oxidative C–H functionalization is reported. A commercially available quinone organocatalyst is employed to promote the aerobic oxidation of primary amines to the corresponding N‐protected imines, which are then trapped in situ with an appropriate nucleophile to give access to versatile functionalized amines in good to excellent yields (70–90 %).