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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...

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Autores principales: Qiao, Yupu, Si, Tuda, Yang, Ming-Hsiu, Altman, Ryan A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
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.
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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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