Issue 17, 2018
From the journal:

Organic & Biomolecular Chemistry

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters via C–N bond activation†

Weijie Yu,a   Shuwu Yang,a   Fei Xiong, ORCID logo a   Tianxiang Fan,a   Yan Feng,a   Yuanyuan Huang,a   Junkai Fu ORCID logo *b  and  Tao Wang ORCID logo *a  

* Corresponding authors

a National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang 330022, Jiangxi, P. R. China
E-mail: wangtao@jxnu.edu.cn

b Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China
E-mail: fujk109@nenu.edu.cn

Abstract

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C–N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.

Graphical abstract: Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters via C–N bond activation

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Article information

DOI
https://doi.org/10.1039/C8OB00488A
Article type
Communication
Submitted
27 Feb 2018
Accepted
03 Apr 2018
First published
04 Apr 2018

Org. Biomol. Chem., 2018,16, 3099-3103

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Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters via C–N bond activation

W. Yu, S. Yang, F. Xiong, T. Fan, Y. Feng, Y. Huang, J. Fu and T. Wang, Org. Biomol. Chem., 2018, 16, 3099 DOI: 10.1039/C8OB00488A

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