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Ligand free copper(i)-catalyzed synthesis of diaryl ether with Cs2CO3via a free radical path†
Mei-Chun Tseng,I-Jui Hsu,Chien-Chung Han,Shin-Guang Shyu
Dalton Transactions Pub Date : 03/31/2015 00:00:00 , DOI:10.1039/C5DT00151J
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.

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