Issue 7, 2015
From the journal:

Chemical Communications

Palladium(ii)-catalyzed meta-selective direct arylation of O-β-naphthyl carbamate†

Jingchang Zhang,a   Qingwen Liu,a   Xufei Liu,b   Suoqin Zhang,*a   Pingping Jiang,a   Yanxiang Wang,a   Shengyuan Luo,a   Yang Lia  and  Qifeng Wang*ab  

* Corresponding authors

a International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China
E-mail: wangqifeng@jlu.edu.cn, zhangsq@jlu.edu.cn

b State Grid Jilin Province Electric Power Research Institute, 4433 Renmin Street, Changchun 130021, China

Abstract

Selective meta-arylation of O-β-naphthyl carbamate has been accomplished using Pd(OAc)2 as a catalyst precursor and K2S2O8 with AgOAc as the oxidant. A range of aryl boronic acids could be introduced in moderate to good yields. Mechanistic investigation shows that the carbamate substituent has a unique effect and the reaction undergoes an ortho-carbometallation/meta-direct arylation process.

Graphical abstract: Palladium(ii)-catalyzed meta-selective direct arylation of O-β-naphthyl carbamate

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Article information

DOI
https://doi.org/10.1039/C4CC07997C
Article type
Communication
Submitted
09 Oct 2014
Accepted
20 Nov 2014
First published
20 Nov 2014

Chem. Commun., 2015,51, 1297-1300

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Palladium(II)-catalyzed meta-selective direct arylation of O-β-naphthyl carbamate

J. Zhang, Q. Liu, X. Liu, S. Zhang, P. Jiang, Y. Wang, S. Luo, Y. Li and Q. Wang, Chem. Commun., 2015, 51, 1297 DOI: 10.1039/C4CC07997C

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