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o-Naphthoquinone-Catalyzed Aerobic Oxidation of Amines to (Ket)imines: A Modular Catalyst Approach.

Authors :
Goriya Y
Kim HY
Oh K
Source :
Organic letters [Org Lett] 2016 Oct 07; Vol. 18 (19), pp. 5174-5177. Date of Electronic Publication: 2016 Sep 28.
Publication Year :
2016

Abstract

A modular aerobic oxidation of amines to imines has been achieved using an ortho-naphthoquinone (o-NQ) catalyst. The cooperative catalyst system of o-NQ and Cu(OAc) <subscript>2</subscript> enabled the formation of homocoupled imines from benzylamines, while the presence of TFA helped the formation of cross-coupled imines in excellent yields. The current mild aerobic oxidation protocol could also be applied to the oxidation of secondary amines to imines or ketimines with the help of cocatalyst, Ag <subscript>2</subscript> CO <subscript>3</subscript> , with excellent yields.

Details

Language :
English
ISSN :
1523-7052
Volume :
18
Issue :
19
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
27681834
Full Text :
https://doi.org/10.1021/acs.orglett.6b02697