Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides

A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rate...

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Autores principales: Kaplan, Peter T, Lloyd, Jessica A, Chin, Mason T, Vicic, David A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5687013/
https://www.ncbi.nlm.nih.gov/pubmed/29181108
http://dx.doi.org/10.3762/bjoc.13.225
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author Kaplan, Peter T
Lloyd, Jessica A
Chin, Mason T
Vicic, David A
author_facet Kaplan, Peter T
Lloyd, Jessica A
Chin, Mason T
Vicic, David A
author_sort Kaplan, Peter T
collection PubMed
description A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rates of the reactions. Interestingly, differences in reactivity were observed when a well-defined [LCuCF(3)] complex was employed directly or generated in situ from precursors by published reports. Relative reactivities were also found to highly dependent on the nature of the iodoarenes.
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spelling pubmed-56870132017-11-27 Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides Kaplan, Peter T Lloyd, Jessica A Chin, Mason T Vicic, David A Beilstein J Org Chem Full Research Paper A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rates of the reactions. Interestingly, differences in reactivity were observed when a well-defined [LCuCF(3)] complex was employed directly or generated in situ from precursors by published reports. Relative reactivities were also found to highly dependent on the nature of the iodoarenes. Beilstein-Institut 2017-10-30 /pmc/articles/PMC5687013/ /pubmed/29181108 http://dx.doi.org/10.3762/bjoc.13.225 Text en Copyright © 2017, Kaplan et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Kaplan, Peter T
Lloyd, Jessica A
Chin, Mason T
Vicic, David A
Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
title Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
title_full Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
title_fullStr Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
title_full_unstemmed Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
title_short Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
title_sort comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5687013/
https://www.ncbi.nlm.nih.gov/pubmed/29181108
http://dx.doi.org/10.3762/bjoc.13.225
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