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

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초록

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)2 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, Ag2CO3, with excellent yields.

키워드

PRIMARY ALIPHATIC-AMINES; BOVINE PLASMA AMINE; CHEMICAL-PROPERTIES; ORTHO-QUINONES; COENZYME PQQ; COFACTOR TTQ; MODEL; OXIDASES; BENZYLAMINE; MECHANISM
제목
o-Naphthoquinone-Catalyzed Aerobic Oxidation of Amines to (Ket)imines: A Modular Catalyst Approach
저자
Goriya, Yogesh; Kim, Hun Young; Oh, Kyungsoo
DOI
10.1021/acs.orglett.6b02697
발행일
2016-10
유형
Article
저널명
Organic Letters
권
18
호
19
페이지
5174 ~ 5177