Issue 2, 2012
From the journal:

Green Chemistry

Bio-based synthesis of secondary arylamines from (−)-shikimic acid†

Wei Wu,ab   Yong Zou,*a   Yu Chen,ab   Jun Li,c   Zeliang Lv,ab   Wen Wei,a   Tongkun Huanga  and  Xianke Liuab  

* Corresponding authors

a Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, P. R. of China
E-mail: zou_jinan@163.com
Fax: +86(20)85231119
Tel: +86(20)85231309

b Graduate School of Chinese Academy of Sciences, Beijing, P. R. of China

c Second Affiliated Hospital, College of Medicine, Zhejiang University, Zhejiang, P. R. of China

Abstract

A specific family of secondary arylamines, including diarylamines and arylalkylamines have been synthesized in good yields starting from the renewable and biomass-based feedstock (−)-shikimic acid (1). The tandem cross-coupling and aromatization reactions between primary amines and the intermediate (−)-methyl-3-dehydroshikimate (3) are crucial for realizing this strategy. The application of arylamines and alkylamines provided 3-arylamino-4-hydroxybenzoates (5) and 3,4-dihydroxy-5-alkylaminobenzoates (7) respectively via a selective dehydration or dehydrogenation process.

Graphical abstract: Bio-based synthesis of secondary arylamines from (−)-shikimic acid

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Article information

DOI
https://doi.org/10.1039/C1GC16162H
Article type
Paper
Submitted
19 Sep 2011
Accepted
27 Oct 2011
First published
06 Dec 2011

Green Chem., 2012,14, 363-370

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Bio-based synthesis of secondary arylamines from (−)-shikimic acid

W. Wu, Y. Zou, Y. Chen, J. Li, Z. Lv, W. Wei, T. Huang and X. Liu, Green Chem., 2012, 14, 363 DOI: 10.1039/C1GC16162H

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