Ligand free copper(I)-catalyzed synthesis of diaryl ether with Cs2CO3via a free radical path

Hong-Jie Chen; Mei-Chun Tseng; I-Jui Hsu; Wei-Ting Chen; Chien-Chung Han; Shin-Guang Shyu

doi:10.1039/C5DT00151J

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Ligand free copper(i)-catalyzed synthesis of diaryl ether with Cs₂CO₃via a free radical path†

Hong-Jie Chen,^ab Mei-Chun Tseng,^a I-Jui Hsu,^c Wei-Ting Chen,^ac Chien-Chung Han*^b and Shin-Guang Shyu*^a

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* Corresponding authors

^a Institute of Chemistry, Academia Sinica, 128 Academia Road Sec. 2, Nankang, Taipei 115, Taiwan, Republic of China
E-mail: sgshyu@chem.sinica.edu.tw
Fax: +886-2-2783-1237
Tel: +886-2-2789-8593

^b Department of Chemistry, National Tsing Hua University, 101, Sec 2, Kuang-Fu Rd, Hsinchu 30013, Taiwan, Republic of China

^c Department of Molecular Science and Engineering, National Taipei University of Technology, 1, Sec. 3, Zhongxiao E Road, Taipei 10608, Taiwan, Republic of China

Abstract

Complexes [Cu(I)(2,4-dimethylphenoxy)₂]⁻ (A) and [Cu(II)(2,4-dimethylphenoxy)₂(p-tolyl)]⁻ (B) were observed by in situ electrospray ionization mass spectrometry (ESI-MS) analysis of the ligand free copper(I)-catalyzed C–O coupling reaction using Cs₂CO₃ under the catalytic reaction conditions indicating that they could be intermediates in the reaction. The radical scavenger cumene retarded the reaction. Catalytic cycles involving a free radical path are proposed based on these observations.

This article is part of the themed collection: Earth Abundant Element Compounds in Homogeneous Catalysis

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Article information

DOI: https://doi.org/10.1039/C5DT00151J
Article type: Communication
Submitted: 13 Jan 2015
Accepted: 24 Mar 2015
First published: 31 Mar 2015

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Dalton Trans., 2015,44, 12086-12090

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Ligand free copper(I)-catalyzed synthesis of diaryl ether with Cs₂CO₃via a free radical path

H. Chen, M. Tseng, I. Hsu, W. Chen, C. Han and S. Shyu, Dalton Trans., 2015, 44, 12086 DOI: 10.1039/C5DT00151J

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