Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Nakamura, Yuzo, Fujiu, Motohiro, Murase, Tatsuya, Itoh, Yoshimitsu, Serizawa, Hiroki, Aikawa, Kohsuke, Mikami, Koichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
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
_version_ 1782296560639410176
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
work_keys_str_mv AT nakamurayuzo cucatalyzedtrifluoromethylationofaryliodideswithtrifluoromethylzincreagentpreparedinsitufromtrifluoromethyliodide
AT fujiumotohiro cucatalyzedtrifluoromethylationofaryliodideswithtrifluoromethylzincreagentpreparedinsitufromtrifluoromethyliodide
AT murasetatsuya cucatalyzedtrifluoromethylationofaryliodideswithtrifluoromethylzincreagentpreparedinsitufromtrifluoromethyliodide
AT itohyoshimitsu cucatalyzedtrifluoromethylationofaryliodideswithtrifluoromethylzincreagentpreparedinsitufromtrifluoromethyliodide
AT serizawahiroki cucatalyzedtrifluoromethylationofaryliodideswithtrifluoromethylzincreagentpreparedinsitufromtrifluoromethyliodide
AT aikawakohsuke cucatalyzedtrifluoromethylationofaryliodideswithtrifluoromethylzincreagentpreparedinsitufromtrifluoromethyliodide
AT mikamikoichi cucatalyzedtrifluoromethylationofaryliodideswithtrifluoromethylzincreagentpreparedinsitufromtrifluoromethyliodide