A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds

Yaxin Wang; Guo-Xing Li; Guohui Yang; Gang He; Gong Chen

doi:10.1039/C5SC04169D

A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds†

Yaxin Wang,^a Guo-Xing Li,^a Guohui Yang,^a Gang He^a and Gong Chen*^ab

* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China
E-mail: gongchen@nankai.edu.cn

^b Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802, USA
E-mail: guc11@psu.edu

Abstract

A highly tunable radical-mediated reaction system for the functionalization of tertiary aliphatic C–H bonds was developed. Reactions of various substrates with the Zhdankin azidoiodane reagent 1, Ru(bpy)₃Cl₂, and visible light irradiation at room temperature gave C–H azidated or halogenated products in an easily controllable fashion. These reactions are efficient, selective, and compatible with complex substrates. They provide a potentially valuable tool for selectively labeling tertiary C–H bonds of organic and biomolecules with tags of varied chemical and biophysical properties for comparative functional studies.

This article is part of the themed collection: Top 50 Articles of 2016: Organic Chemistry

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DOI: https://doi.org/10.1039/C5SC04169D
Article type: Edge Article
Submitted: 03 Nov 2015
Accepted: 09 Jän 2016
First published: 11 Jän 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2016,7, 2679-2683

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A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds

Y. Wang, G. Li, G. Yang, G. He and G. Chen, Chem. Sci., 2016, 7, 2679 DOI: 10.1039/C5SC04169D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Science

A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds†

Abstract

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A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds

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