Issue 23, 2011
From the journal:

Chemical Communications

A copper(ii) complex as an intermediate of copper(i)-catalyzed C–N cross coupling of N-phenylaniline with aryl halide by in situESI-MS study†

Chia-Kai Tseng,ab   Mei-Chun Tseng,a   Chien-Chung Han*b  and  Shin-Guang Shyu*a  

* Corresponding authors

a Institute of Chemistry, Academia Sinica, 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, Hsinchu, Taiwan, Republic of China
E-mail: cchan@mx.nthu.edu.tw
Fax: +886-3-5711082
Tel: +886-3-5724998

Abstract

Complexes [Cu(NPh2)2]−, [Cu(NPh2)I]− and K[Cu(phen)(NPh2) (p-tolyl)]+ were observed by in situelectrospray ionization mass spectrometry (ESI-MS) analysis of the copper(I)-catalyzed C–N coupling reaction under the catalytic reaction condition indicating that they are intermediates in the reaction. A catalytic cycle composed of a free radical path and a 2e oxidative addition path is proposed based on these observations.

Graphical abstract: A copper(ii) complex as an intermediate of copper(i)-catalyzed C–N cross coupling of N-phenylaniline with aryl halide by in situESI-MS study

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Article information

DOI
https://doi.org/10.1039/C1CC11906K
Article type
Communication
Submitted
04 Apr 2011
Accepted
19 Apr 2011
First published
05 May 2011

Chem. Commun., 2011,47, 6686-6688

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A copper(II) complex as an intermediate of copper(I)-catalyzed C–N cross coupling of N-phenylaniline with aryl halide by in situESI-MS study

C. Tseng, M. Tseng, C. Han and S. Shyu, Chem. Commun., 2011, 47, 6686 DOI: 10.1039/C1CC11906K

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