Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex

A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Prel...

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Published inAngewandte Chemie International Edition Vol. 54; no. 46; pp. 13734 - 13738
Main Authors Cheng, Li-Jie, Cordier, Christopher J.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 09.11.2015
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
alkynes
carbene ligands
Carbenes
Catalysis
Catalysts
Cationic
Chemistry
Chemistry, Multidisciplinary
Communications
Copper
Fluorides
Fluorination
fluorine
Formations
homogeneous catalysis
Physical Sciences
Science & Technology
HALIDES
alkynes
carbene ligands
SUBSTITUTION-REACTIONS
MEDICINAL CHEMISTRY
ALCOHOLS
CYCLOADDITION
AMINATION
ALLYLIC FLUORIDES
BETA-KETOESTERS
homogeneous catalysis
ESTERS
copper
ALLENYLIDENE
fluorine
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Abstract A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and that cationic species are involved. A carbene can: A Cu(NHC)‐catalyzed nucleophilic fluorination of propargylic electrophiles was found to be suitable for the synthesis of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes (see scheme; NHC=N‐heterocyclic carbene, Ms=methanesulfonyl, Ts=p‐toluenesulfonyl). Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and involves cationic species.
AbstractList A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and that cationic species are involved.
A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and that cationic species are involved. A carbene can: A Cu(NHC)‐catalyzed nucleophilic fluorination of propargylic electrophiles was found to be suitable for the synthesis of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes (see scheme; NHC=N‐heterocyclic carbene, Ms=methanesulfonyl, Ts=p‐toluenesulfonyl). Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and involves cationic species.
A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and that cationic species are involved. A carbene can: A Cu(NHC)-catalyzed nucleophilic fluorination of propargylic electrophiles was found to be suitable for the synthesis of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes (see scheme; NHC=N-heterocyclic carbene, Ms=methanesulfonyl, Ts=p-toluenesulfonyl). Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and involves cationic species.
A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and that cationic species are involved.A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Preliminary mechanistic investigations suggest that fluorination proceeds via copper acetylides and that cationic species are involved.
Author Cordier, Christopher J.
Cheng, Li-Jie
Author_xml – sequence: 1
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  surname: Cheng
  fullname: Cheng, Li-Jie
  organization: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ (UK)
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  givenname: Christopher J.
  surname: Cordier
  fullname: Cordier, Christopher J.
  email: ccordier@imperial.ac.uk
  organization: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ (UK)
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ContentType Journal Article
Copyright 2015 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. 2015
Copyright_xml – notice: 2015 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
– notice: 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
– notice: 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. 2015
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Keywords HALIDES
alkynes
carbene ligands
SUBSTITUTION-REACTIONS
MEDICINAL CHEMISTRY
ALCOHOLS
CYCLOADDITION
AMINATION
ALLYLIC FLUORIDES
BETA-KETOESTERS
homogeneous catalysis
ESTERS
copper
ALLENYLIDENE
fluorine
Language English
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2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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Snippet A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the...
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StartPage 13734
SubjectTerms alkynes
carbene ligands
Carbenes
Catalysis
Catalysts
Cationic
Chemistry
Chemistry, Multidisciplinary
Communications
Copper
Fluorides
Fluorination
fluorine
Formations
homogeneous catalysis
Physical Sciences
Science & Technology
Title Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex
URI https://api.istex.fr/ark:/67375/WNG-RSLZDTLR-R/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201506882
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https://www.ncbi.nlm.nih.gov/pubmed/26403935
https://www.proquest.com/docview/1728717219
https://www.proquest.com/docview/1730021828
https://www.proquest.com/docview/1770371750
https://pubmed.ncbi.nlm.nih.gov/PMC4648036
Volume 54
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