Issue 15, 2014
From the journal:

RSC Advances

Oxidative ortho-amino-methylation of phenols via C–H and C–C bond cleavage†

Wenbo Sun,a   Huacan Lin,a   Wenyu Zhou*b  and  Zigang Li*a  

* Corresponding authors

a Key laboratory of Chemical Genetics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen University Town, Shenzhen, P.R.China
E-mail: lizg@pkusz.edu.cn
Fax: +86-755-2603-3174
Tel: +86-755-2603-3616

b Shenzhen Second People's Hospital, 3002, ShunGang West Road, Shenzhen, Guangdong, P.R.China
E-mail: drzhouwenyu@163.com
Fax: +86-755-8336-6388
Tel: +86-755-8307-3866

Abstract

Initiated by CCl3Br, phenols undergo efficient ortho-selective oxidative cross dehydrogenative coupling (CDC) with trimethylamine. When tetramethylethylenediamine (TMEDA) is used instead of trimethylamine, oxidative carbon–carbon activation coupling (CAC) could occur to give the same salicylamines together with CDC by-products. These reactions are accelerated by a gold salt.

Graphical abstract: Oxidative ortho-amino-methylation of phenols via C–H and C–C bond cleavage

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Article information

DOI
https://doi.org/10.1039/C3RA46373G
Article type
Communication
Submitted
04 Nov 2013
Accepted
27 Nov 2013
First published
28 Nov 2013

RSC Adv., 2014,4, 7491-7494

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Oxidative ortho-amino-methylation of phenols via C–H and C–C bond cleavage

W. Sun, H. Lin, W. Zhou and Z. Li, RSC Adv., 2014, 4, 7491 DOI: 10.1039/C3RA46373G

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