Issue 21, 2021
From the journal:

Organic Chemistry Frontiers

Divergent synthesis of unsymmetrical azobenzenes via Cu-catalyzed C–N coupling†

Yuzhou Wang,a   Rongrong Xie,a   Lingyu Huang,a   Ya-Nan Tian,a   Shihai Lv,a   Xiangfei Konga  and  Shiqing Li ORCID logo *a  

* Corresponding authors

a Guangxi Key Laboratory of Electrochemical and Magneto-Chemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China
E-mail: lisq@glut.edu.cn

Abstract

An efficient, one-pot, and low-cost metal-catalyzed tandem Chan–Lam coupling/deprotection/oxidation reaction to access unsymmetrical azobenzenes was developed. The phthaloyl group was automatically released from the rest of the molecule under the conditions of the basic catalytic system of this protocol, without extra steps for deprotection. A variety of azobenzenes were easily obtained using this C–N coupling strategy, without precautions against generating undesired azo by-products. Moreover, an unusual, three-component and domino Ullmann/Chan–Lam/deprotection/oxidation reaction proceeded smoothly to assemble azobenzenes in good yields, where phthalic hydrazide served as a source of N2.

Graphical abstract: Divergent synthesis of unsymmetrical azobenzenes via Cu-catalyzed C–N coupling

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Article information

DOI
https://doi.org/10.1039/D1QO00945A
Article type
Research Article
Submitted
25 Jun 2021
Accepted
13 Aug 2021
First published
14 Aug 2021

Org. Chem. Front., 2021,8, 5962-5967

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Divergent synthesis of unsymmetrical azobenzenes via Cu-catalyzed C–N coupling

Y. Wang, R. Xie, L. Huang, Y. Tian, S. Lv, X. Kong and S. Li, Org. Chem. Front., 2021, 8, 5962 DOI: 10.1039/D1QO00945A

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