Organocatalytic amination of alkyl ethers via n-Bu4NI/t-BuOOH-mediated intermolecular oxidative C(sp3)–N bond formation: novel synthesis of hemiaminal ethers

Longyang Dian; Sisi Wang; Daisy Zhang-Negrerie; Yunfei Du; Kang Zhao

doi:10.1039/C4CC05758A

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Organocatalytic amination of alkyl ethers via n-Bu₄NI/t-BuOOH-mediated intermolecular oxidative C(sp³)–N bond formation: novel synthesis of hemiaminal ethers†

Longyang Dian,^a Sisi Wang,^a Daisy Zhang-Negrerie,^a Yunfei Du*^ab and Kang Zhao^a

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* Corresponding authors

^a School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China
E-mail: duyunfeier@tju.edu.cn
Fax: +86-22-27404031
Tel: +86-22-27404031

^b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China

Abstract

A novel method for constructing the hemiaminal ether framework under metal-free conditions has been developed. It involves direct organocatalytic amination of alkyl ethers through intermolecular oxidative C(sp³)–N bond formation, with t-BuOOH being the oxidant and n-Bu₄NI as the catalyst.

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Article information

DOI: https://doi.org/10.1039/C4CC05758A
Article type: Communication
Submitted: 24 Jul 2014
Accepted: 12 Aug 2014
First published: 13 Aug 2014

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Chem. Commun., 2014,50, 11738-11741

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Organocatalytic amination of alkyl ethers via n-Bu₄NI/t-BuOOH-mediated intermolecular oxidative C(sp³)–N bond formation: novel synthesis of hemiaminal ethers

L. Dian, S. Wang, D. Zhang-Negrerie, Y. Du and K. Zhao, Chem. Commun., 2014, 50, 11738 DOI: 10.1039/C4CC05758A

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