Issue 36, 2013
From the journal:

Organic & Biomolecular Chemistry

An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters†

Cheng Qian,a   Jiayan Chen,a   Meiqin Fu,a   Shiya Zhu,a   Wen-Hua Chen,b   Huanfeng Jianga  and  Wei Zeng*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, P. R. China
E-mail: zengwei@scut.edu.cn

b School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, P. R. China

Abstract

The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation.

Graphical abstract: An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters

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Article information

DOI
https://doi.org/10.1039/C3OB41011K
Article type
Paper
Submitted
15 May 2013
Accepted
12 Jul 2013
First published
16 Jul 2013

Org. Biomol. Chem., 2013,11, 6013-6022

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An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters

C. Qian, J. Chen, M. Fu, S. Zhu, W. Chen, H. Jiang and W. Zeng, Org. Biomol. Chem., 2013, 11, 6013 DOI: 10.1039/C3OB41011K

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