Issue 35, 2016, Issue in Progress
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RSC Advances

Combined experimental/theoretical study of d-glucosamine promoted Ullmann-type C–N coupling catalyzed by copper(i): does amino really count?†

Xin Ge,ab   Xinzhi Chen,b   Chao Qian*b  and  Shaodong Zhou*c  

* Corresponding authors

a School of Chemical and Material Engineering, Jiangnan University, Wuxi, P. R. China

b Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, P. R. China
E-mail: qianchao@zju.edu.cn

c Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 135, 10623 Berlin, Germany
E-mail: shaodong.zhou@campus.tu-berlin.de

Abstract

Ullmann type C–N coupling reaction catalyzed by copper(I) with D-glucosamine derivatives as promoters was studied by means of combined experimental/theoretical investigation. The catalytic role of D-glucosamine was addressed. In contrast with previous speculations, the amino group may not count in the catalytic cycle in which the oxidative addition/reductive elimination mechanism works. Experimental results are in good agreement with theoretical findings. Extensive work indicates the wide applicability of the C–N coupling strategy exploited in this work.

Graphical abstract: Combined experimental/theoretical study of d-glucosamine promoted Ullmann-type C–N coupling catalyzed by copper(i): does amino really count?

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Article information

DOI
https://doi.org/10.1039/C6RA03015G
Article type
Paper
Submitted
01 Feb 2016
Accepted
14 Mar 2016
First published
16 Mar 2016

RSC Adv., 2016,6, 29638-29645

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Combined experimental/theoretical study of D-glucosamine promoted Ullmann-type C–N coupling catalyzed by copper(I): does amino really count?

X. Ge, X. Chen, C. Qian and S. Zhou, RSC Adv., 2016, 6, 29638 DOI: 10.1039/C6RA03015G

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