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

Yogesh Goriya, Hun Young Kim* and Kyungsoo Oh*

*Center for Metareceptome Research, College of Pharmacy, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea, Email: hunykimcau.ac.kr, kyungsooohcau.ac.kr

Y. Goriya, H. Y. Kim, K. Oh, Org. Lett., 2016, 18, 5174-5177.

DOI: 10.1021/acs.orglett.6b02697 (free Supporting Information)


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Abstract

A modular aerobic oxidation of amines to imines has been achieved using an ortho-naphthoquinone (o-NQ) catalyst. Whereas the cooperative catalyst system of o-NQ and Cu(OAc)2 provided homocoupled imines from benzylamines, the presence of TFA helped the formation of cross-coupled imines in excellent yields. The oxidation of secondary amines to imines or ketimines is facilitated with the help of Ag2CO3 as cocatalyst.


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Key Words

oxygen, organocatalysis, imines


ID: J54-Y2016