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Metal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones
[Image: see text] The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120972/ https://www.ncbi.nlm.nih.gov/pubmed/25001876 http://dx.doi.org/10.1021/jo501289v |
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author | Qiao, Yupu Si, Tuda Yang, Ming-Hsiu Altman, Ryan A. |
author_facet | Qiao, Yupu Si, Tuda Yang, Ming-Hsiu Altman, Ryan A. |
author_sort | Qiao, Yupu |
collection | PubMed |
description | [Image: see text] The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing β,β,β-trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability. |
format | Online Article Text |
id | pubmed-4120972 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-41209722015-07-08 Metal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones Qiao, Yupu Si, Tuda Yang, Ming-Hsiu Altman, Ryan A. J Org Chem [Image: see text] The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing β,β,β-trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability. American Chemical Society 2014-07-08 2014-08-01 /pmc/articles/PMC4120972/ /pubmed/25001876 http://dx.doi.org/10.1021/jo501289v Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Qiao, Yupu Si, Tuda Yang, Ming-Hsiu Altman, Ryan A. Metal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones |
title | Metal-Free Trifluoromethylation
of Aromatic and Heteroaromatic
Aldehydes and Ketones |
title_full | Metal-Free Trifluoromethylation
of Aromatic and Heteroaromatic
Aldehydes and Ketones |
title_fullStr | Metal-Free Trifluoromethylation
of Aromatic and Heteroaromatic
Aldehydes and Ketones |
title_full_unstemmed | Metal-Free Trifluoromethylation
of Aromatic and Heteroaromatic
Aldehydes and Ketones |
title_short | Metal-Free Trifluoromethylation
of Aromatic and Heteroaromatic
Aldehydes and Ketones |
title_sort | metal-free trifluoromethylation
of aromatic and heteroaromatic
aldehydes and ketones |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120972/ https://www.ncbi.nlm.nih.gov/pubmed/25001876 http://dx.doi.org/10.1021/jo501289v |
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