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Heterogeneous Platinum‐Catalyzed CH Perfluoroalkylation of Arenes and Heteroarenes

Fluorinated organic compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple proto... Full description

Journal Title: Angewandte Chemie International Edition 27 March 2015, Vol.54(14), pp.4320-4324
Main Author: He, Lin
Other Authors: Natte, Kishore , Rabeah, Jabor , Taeschler, Christoph , Neumann, Helfried , Brückner, Angelika , Beller, Matthias
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201411066
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recordid: wj10.1002/anie.201411066
title: Heterogeneous Platinum‐Catalyzed CH Perfluoroalkylation of Arenes and Heteroarenes
format: Article
creator:
  • He, Lin
  • Natte, Kishore
  • Rabeah, Jabor
  • Taeschler, Christoph
  • Neumann, Helfried
  • Brückner, Angelika
  • Beller, Matthias
subjects:
  • Ch Activation
  • Heterogeneous Catalysis
  • Platinum
  • Radicals
  • Synthetic Methods
ispartof: Angewandte Chemie International Edition, 27 March 2015, Vol.54(14), pp.4320-4324
description: Fluorinated organic compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple protocol for the direct CH perfluoroalkylation of (hetero)arenes with RI or RBr has been developed, using a robust supported platinum catalyst. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of the catalyst make this method attractive for the synthesis of a variety of perfluoroalkyl‐substituted aromatic compounds. Preliminary mechanistic studies revealed the formation of radicals to be crucial in the reaction system. The efficient and versatile title reaction is based on the radical reactivity of perfluoroalkyl halides. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of catalyst make this protocol attractive for the economic synthesis of perfluoroalkyl‐group‐substituted aromatic compounds.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201411066
fulltext: fulltext
issn:
  • 1433-7851
  • 14337851
  • 1521-3773
  • 15213773
url: Link


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titleHeterogeneous Platinum‐Catalyzed CH Perfluoroalkylation of Arenes and Heteroarenes
creatorHe, Lin ; Natte, Kishore ; Rabeah, Jabor ; Taeschler, Christoph ; Neumann, Helfried ; Brückner, Angelika ; Beller, Matthias
ispartofAngewandte Chemie International Edition, 27 March 2015, Vol.54(14), pp.4320-4324
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subjectCh Activation ; Heterogeneous Catalysis ; Platinum ; Radicals ; Synthetic Methods
descriptionFluorinated organic compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple protocol for the direct CH perfluoroalkylation of (hetero)arenes with RI or RBr has been developed, using a robust supported platinum catalyst. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of the catalyst make this method attractive for the synthesis of a variety of perfluoroalkyl‐substituted aromatic compounds. Preliminary mechanistic studies revealed the formation of radicals to be crucial in the reaction system. The efficient and versatile title reaction is based on the radical reactivity of perfluoroalkyl halides. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of catalyst make this protocol attractive for the economic synthesis of perfluoroalkyl‐group‐substituted aromatic compounds.
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titleHeterogeneous Platinum‐Catalyzed CH Perfluoroalkylation of Arenes and Heteroarenes
descriptionFluorinated organic compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple protocol for the direct CH perfluoroalkylation of (hetero)arenes with RI or RBr has been developed, using a robust supported platinum catalyst. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of the catalyst make this method attractive for the synthesis of a variety of perfluoroalkyl‐substituted aromatic compounds. Preliminary mechanistic studies revealed the formation of radicals to be crucial in the reaction system. The efficient and versatile title reaction is based on the radical reactivity of perfluoroalkyl halides. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of catalyst make this protocol attractive for the economic synthesis of perfluoroalkyl‐group‐substituted aromatic compounds.
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titleHeterogeneous Platinum‐Catalyzed CH Perfluoroalkylation of Arenes and Heteroarenes
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abstractFluorinated organic compounds are gaining increasing interest for life science applications. The replacement of hydrogen in arenes or heteroarenes by a perfluoroalkyl group has a profound influence on the physical and biological properties of such building blocks. Here, an operationally simple protocol for the direct CH perfluoroalkylation of (hetero)arenes with RI or RBr has been developed, using a robust supported platinum catalyst. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of the catalyst make this method attractive for the synthesis of a variety of perfluoroalkyl‐substituted aromatic compounds. Preliminary mechanistic studies revealed the formation of radicals to be crucial in the reaction system. The efficient and versatile title reaction is based on the radical reactivity of perfluoroalkyl halides. The ready availability of the starting materials, the excellent substrate tolerance, and the reusability of catalyst make this protocol attractive for the economic synthesis of perfluoroalkyl‐group‐substituted aromatic compounds.
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doi10.1002/anie.201411066
pages4320-4324
date2015-03-27