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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Autores principales: Cheng, Li-Jie, Cordier, Christopher J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648036/
https://www.ncbi.nlm.nih.gov/pubmed/26403935
http://dx.doi.org/10.1002/anie.201506882
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author Cheng, Li-Jie
Cordier, Christopher J
author_facet Cheng, Li-Jie
Cordier, Christopher J
author_sort Cheng, Li-Jie
collection PubMed
description 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.
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spelling pubmed-46480362015-11-24 Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex Cheng, Li-Jie Cordier, Christopher J Angew Chem Int Ed Engl Communications 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. WILEY-VCH Verlag 2015-11-09 2015-09-25 /pmc/articles/PMC4648036/ /pubmed/26403935 http://dx.doi.org/10.1002/anie.201506882 Text en © 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. https://creativecommons.org/licenses/by/4.0/ © 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.
spellingShingle Communications
Cheng, Li-Jie
Cordier, Christopher J
Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex
title Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex
title_full Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex
title_fullStr Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex
title_full_unstemmed Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex
title_short Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex
title_sort catalytic nucleophilic fluorination of secondary and tertiary propargylic electrophiles with a copper–n-heterocyclic carbene complex
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648036/
https://www.ncbi.nlm.nih.gov/pubmed/26403935
http://dx.doi.org/10.1002/anie.201506882
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AT cordierchristopherj catalyticnucleophilicfluorinationofsecondaryandtertiarypropargylicelectrophileswithacoppernheterocycliccarbenecomplex

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