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

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)(3)Cl(2), and visible light irradiation at room temperature gave C–H azidated or halogenated prod...

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Autores principales: Wang, Yaxin, Li, Guo-Xing, Yang, Guohui, He, Gang, Chen, Gong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5477033/
https://www.ncbi.nlm.nih.gov/pubmed/28660040
http://dx.doi.org/10.1039/c5sc04169d
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author Wang, Yaxin
Li, Guo-Xing
Yang, Guohui
He, Gang
Chen, Gong
author_facet Wang, Yaxin
Li, Guo-Xing
Yang, Guohui
He, Gang
Chen, Gong
author_sort Wang, Yaxin
collection PubMed
description 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)(3)Cl(2), 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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spelling pubmed-54770332017-06-28 A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds Wang, Yaxin Li, Guo-Xing Yang, Guohui He, Gang Chen, Gong Chem Sci Chemistry 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)(3)Cl(2), 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. Royal Society of Chemistry 2016-04-01 2016-01-11 /pmc/articles/PMC5477033/ /pubmed/28660040 http://dx.doi.org/10.1039/c5sc04169d Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Wang, Yaxin
Li, Guo-Xing
Yang, Guohui
He, Gang
Chen, Gong
A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds
title A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds
title_full A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds
title_fullStr A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds
title_full_unstemmed A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds
title_short A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C–H bonds
title_sort visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic c–h bonds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5477033/
https://www.ncbi.nlm.nih.gov/pubmed/28660040
http://dx.doi.org/10.1039/c5sc04169d
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