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Directed meta‐Selective Bromination of Arenes with Ruthenium Catalysts

A Ru‐catalyzed direct CH activation/‐bromination of arenes bearing pyridyl, pyrimidyl, and pyrazolyl directing groups has been developed. A series of bromo aryl pyridines and pyrimidines have been synthesized, and further coupling reactions have also been demonstrated for a number of representative... Full description

Journal Title: Angewandte Chemie International Edition 07 December 2015, Vol.54(50), pp.15284-15288
Main Author: Yu, Qingzhen
Other Authors: Hu, Le' An , Wang, Yue , Zheng, Shasha , Huang, Jianhui
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201507100
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recordid: wj10.1002/anie.201507100
title: Directed meta‐Selective Bromination of Arenes with Ruthenium Catalysts
format: Article
creator:
  • Yu, Qingzhen
  • Hu, Le' An
  • Wang, Yue
  • Zheng, Shasha
  • Huang, Jianhui
subjects:
  • Bromination
  • Ch Activation
  • Meta ‐Selective
  • Radical Processes
ispartof: Angewandte Chemie International Edition, 07 December 2015, Vol.54(50), pp.15284-15288
description: A Ru‐catalyzed direct CH activation/‐bromination of arenes bearing pyridyl, pyrimidyl, and pyrazolyl directing groups has been developed. A series of bromo aryl pyridines and pyrimidines have been synthesized, and further coupling reactions have also been demonstrated for a number of representative functionalized arenes. Preliminary mechanistic studies have revealed that this reaction may proceed through radical‐mediated bromination when NBS is utilized as the bromine source. This type of transformation has opened up a new direction for the radical non‐ipso functionalization of metal with regard to future CH activation development that would allow the remote functionalization of aromatic systems. ­ ‐bromination of arenes bearing various pyridyl or pyrimidyl directing groups (DGs) is reported. This procedure is demonstrated in the concise synthesis of Vismodegib, and mechanistic studies suggest that bromination proceeds through radical intermediates.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201507100
fulltext: fulltext
issn:
  • 1433-7851
  • 14337851
  • 1521-3773
  • 15213773
url: Link


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titleDirected meta‐Selective Bromination of Arenes with Ruthenium Catalysts
creatorYu, Qingzhen ; Hu, Le' An ; Wang, Yue ; Zheng, Shasha ; Huang, Jianhui
ispartofAngewandte Chemie International Edition, 07 December 2015, Vol.54(50), pp.15284-15288
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subjectBromination ; Ch Activation ; Meta ‐Selective ; Radical Processes
descriptionA Ru‐catalyzed direct CH activation/‐bromination of arenes bearing pyridyl, pyrimidyl, and pyrazolyl directing groups has been developed. A series of bromo aryl pyridines and pyrimidines have been synthesized, and further coupling reactions have also been demonstrated for a number of representative functionalized arenes. Preliminary mechanistic studies have revealed that this reaction may proceed through radical‐mediated bromination when NBS is utilized as the bromine source. This type of transformation has opened up a new direction for the radical non‐ipso functionalization of metal with regard to future CH activation development that would allow the remote functionalization of aromatic systems. ­ ‐bromination of arenes bearing various pyridyl or pyrimidyl directing groups (DGs) is reported. This procedure is demonstrated in the concise synthesis of Vismodegib, and mechanistic studies suggest that bromination proceeds through radical intermediates.
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titleDirected meta‐Selective Bromination of Arenes with Ruthenium Catalysts
descriptionA Ru‐catalyzed direct CH activation/‐bromination of arenes bearing pyridyl, pyrimidyl, and pyrazolyl directing groups has been developed. A series of bromo aryl pyridines and pyrimidines have been synthesized, and further coupling reactions have also been demonstrated for a number of representative functionalized arenes. Preliminary mechanistic studies have revealed that this reaction may proceed through radical‐mediated bromination when NBS is utilized as the bromine source. This type of transformation has opened up a new direction for the radical non‐ipso functionalization of metal with regard to future CH activation development that would allow the remote functionalization of aromatic systems. ­ ‐bromination of arenes bearing various pyridyl or pyrimidyl directing groups (DGs) is reported. This procedure is demonstrated in the concise synthesis of Vismodegib, and mechanistic studies suggest that bromination proceeds through radical intermediates.
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abstractA Ru‐catalyzed direct CH activation/‐bromination of arenes bearing pyridyl, pyrimidyl, and pyrazolyl directing groups has been developed. A series of bromo aryl pyridines and pyrimidines have been synthesized, and further coupling reactions have also been demonstrated for a number of representative functionalized arenes. Preliminary mechanistic studies have revealed that this reaction may proceed through radical‐mediated bromination when NBS is utilized as the bromine source. This type of transformation has opened up a new direction for the radical non‐ipso functionalization of metal with regard to future CH activation development that would allow the remote functionalization of aromatic systems. ­ ‐bromination of arenes bearing various pyridyl or pyrimidyl directing groups (DGs) is reported. This procedure is demonstrated in the concise synthesis of Vismodegib, and mechanistic studies suggest that bromination proceeds through radical intermediates.
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pubWILEY‐VCH Verlag
doi10.1002/anie.201507100
pages15284-15288
date2015-12-07