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Palladium‐Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br

The CF group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well‐established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less e... Full description

Journal Title: Angewandte Chemie International Edition 18 February 2016, Vol.55(8), pp.2782-2786
Main Author: Natte, Kishore
Other Authors: Jagadeesh, Rajenahally V. , He, Lin , Rabeah, Jabor , Chen, Jianbin , Taeschler, Christoph , Ellinger, Stefan , Zaragoza, Florencio , 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.201511131
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recordid: wj10.1002/anie.201511131
title: Palladium‐Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br
format: Article
creator:
  • Natte, Kishore
  • Jagadeesh, Rajenahally V.
  • He, Lin
  • Rabeah, Jabor
  • Chen, Jianbin
  • Taeschler, Christoph
  • Ellinger, Stefan
  • Zaragoza, Florencio
  • Neumann, Helfried
  • Brückner, Angelika
  • Beller, Matthias
subjects:
  • Arenes
  • C−H Activation
  • Fluorine
  • Palladium
  • Radical Chemistry
ispartof: Angewandte Chemie International Edition, 18 February 2016, Vol.55(8), pp.2782-2786
description: The CF group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well‐established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl‐substituted (hetero)arenes by palladium‐catalyzed C−H functionalization is herein reported. This novel methodology proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity. As examples, trifluoromethylations of biologically important molecules, such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased. : A general and reliable palladium‐catalyzed method for the synthesis of trifluoromethylated (hetero)arenes using CFBr has been developed. The products are isolated in good yields and the reaction proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201511131
fulltext: fulltext
issn:
  • 1433-7851
  • 14337851
  • 1521-3773
  • 15213773
url: Link


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titlePalladium‐Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br
creatorNatte, Kishore ; Jagadeesh, Rajenahally V. ; He, Lin ; Rabeah, Jabor ; Chen, Jianbin ; Taeschler, Christoph ; Ellinger, Stefan ; Zaragoza, Florencio ; Neumann, Helfried ; Brückner, Angelika ; Beller, Matthias
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subjectArenes ; C−H Activation ; Fluorine ; Palladium ; Radical Chemistry
descriptionThe CF group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well‐established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl‐substituted (hetero)arenes by palladium‐catalyzed C−H functionalization is herein reported. This novel methodology proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity. As examples, trifluoromethylations of biologically important molecules, such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased. : A general and reliable palladium‐catalyzed method for the synthesis of trifluoromethylated (hetero)arenes using CFBr has been developed. The products are isolated in good yields and the reaction proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity.
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titlePalladium‐Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br
descriptionThe CF group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well‐established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl‐substituted (hetero)arenes by palladium‐catalyzed C−H functionalization is herein reported. This novel methodology proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity. As examples, trifluoromethylations of biologically important molecules, such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased. : A general and reliable palladium‐catalyzed method for the synthesis of trifluoromethylated (hetero)arenes using CFBr has been developed. The products are isolated in good yields and the reaction proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity.
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titlePalladium‐Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br
authorNatte, Kishore ; Jagadeesh, Rajenahally V. ; He, Lin ; Rabeah, Jabor ; Chen, Jianbin ; Taeschler, Christoph ; Ellinger, Stefan ; Zaragoza, Florencio ; Neumann, Helfried ; Brückner, Angelika ; Beller, Matthias
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abstractThe CF group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well‐established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl‐substituted (hetero)arenes by palladium‐catalyzed C−H functionalization is herein reported. This novel methodology proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity. As examples, trifluoromethylations of biologically important molecules, such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased. : A general and reliable palladium‐catalyzed method for the synthesis of trifluoromethylated (hetero)arenes using CFBr has been developed. The products are isolated in good yields and the reaction proceeds under comparably mild reaction conditions with good regio‐ and chemoselectivity.
doi10.1002/anie.201511131
pages2782-2786
orcididhttp://orcid.org/0000-0001-5709-0965
date2016-02-18