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Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide
The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869366/ https://www.ncbi.nlm.nih.gov/pubmed/24367406 http://dx.doi.org/10.3762/bjoc.9.277 |
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author | Nakamura, Yuzo Fujiu, Motohiro Murase, Tatsuya Itoh, Yoshimitsu Serizawa, Hiroki Aikawa, Kohsuke Mikami, Koichi |
author_facet | Nakamura, Yuzo Fujiu, Motohiro Murase, Tatsuya Itoh, Yoshimitsu Serizawa, Hiroki Aikawa, Kohsuke Mikami, Koichi |
author_sort | Nakamura, Yuzo |
collection | PubMed |
description | The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated products in moderate to high yields. The advantage of this method is that additives such as metal fluoride (MF), which are indispensable to activate silyl groups for transmetallation in the corresponding reactions catalyzed by copper salt by using the Ruppert–Prakash reagents (CF(3)SiR(3)), are not required. |
format | Online Article Text |
id | pubmed-3869366 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-38693662013-12-23 Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide Nakamura, Yuzo Fujiu, Motohiro Murase, Tatsuya Itoh, Yoshimitsu Serizawa, Hiroki Aikawa, Kohsuke Mikami, Koichi Beilstein J Org Chem Letter The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated products in moderate to high yields. The advantage of this method is that additives such as metal fluoride (MF), which are indispensable to activate silyl groups for transmetallation in the corresponding reactions catalyzed by copper salt by using the Ruppert–Prakash reagents (CF(3)SiR(3)), are not required. Beilstein-Institut 2013-11-08 /pmc/articles/PMC3869366/ /pubmed/24367406 http://dx.doi.org/10.3762/bjoc.9.277 Text en Copyright © 2013, Nakamura et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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 | Letter Nakamura, Yuzo Fujiu, Motohiro Murase, Tatsuya Itoh, Yoshimitsu Serizawa, Hiroki Aikawa, Kohsuke Mikami, Koichi Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
title | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
title_full | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
title_fullStr | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
title_full_unstemmed | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
title_short | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
title_sort | cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
topic | Letter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869366/ https://www.ncbi.nlm.nih.gov/pubmed/24367406 http://dx.doi.org/10.3762/bjoc.9.277 |
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