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, Guo Xing Li, Guohui Yang, Gang He, Gong Chen

Chemistry

Research output: Contribution to journal › Article › peer-review

153 Scopus citations

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.

Original language	English (US)
Pages (from-to)	2679-2683
Number of pages	5
Journal	Chemical Science
Volume	7
Issue number	4
DOIs	https://doi.org/10.1039/c5sc04169d
State	Published - Apr 1 2016

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1039/c5sc04169d

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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.",

author = "Yaxin Wang and Li, {Guo Xing} and Guohui Yang and Gang He and Gong Chen",

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AU - Wang, Yaxin

AU - Li, Guo Xing

AU - Yang, Guohui

AU - He, Gang

AU - Chen, Gong

N1 - Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016/4/1

Y1 - 2016/4/1

N2 - 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.

AB - 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.

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

Abstract

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