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Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines
[Image: see text] Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N-dialkylhydrazones and trifluoromethylarenes (CF(3)-arenes). This method relies on selective C–F bond cleavage via reduction of the CF(3)-arene. W...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012270/ https://www.ncbi.nlm.nih.gov/pubmed/36848497 http://dx.doi.org/10.1021/acs.orglett.3c00126 |
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author | Hendy, Cecilia M. Pratt, Cameron J. Jui, Nathan T. Blakey, Simon B. |
author_facet | Hendy, Cecilia M. Pratt, Cameron J. Jui, Nathan T. Blakey, Simon B. |
author_sort | Hendy, Cecilia M. |
collection | PubMed |
description | [Image: see text] Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N-dialkylhydrazones and trifluoromethylarenes (CF(3)-arenes). This method relies on selective C–F bond cleavage via reduction of the CF(3)-arene. We show that a diverse set of CF(3)-arenes and CF(3)-heteroarenes react smoothly with a range of aryl and alkyl hydrazones. The β-difluorobenzylic hydrazine product can be selectively cleaved to form the corresponding benzylic difluoroarylethylamines. |
format | Online Article Text |
id | pubmed-10012270 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-100122702023-03-15 Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines Hendy, Cecilia M. Pratt, Cameron J. Jui, Nathan T. Blakey, Simon B. Org Lett [Image: see text] Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N-dialkylhydrazones and trifluoromethylarenes (CF(3)-arenes). This method relies on selective C–F bond cleavage via reduction of the CF(3)-arene. We show that a diverse set of CF(3)-arenes and CF(3)-heteroarenes react smoothly with a range of aryl and alkyl hydrazones. The β-difluorobenzylic hydrazine product can be selectively cleaved to form the corresponding benzylic difluoroarylethylamines. American Chemical Society 2023-02-27 /pmc/articles/PMC10012270/ /pubmed/36848497 http://dx.doi.org/10.1021/acs.orglett.3c00126 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Hendy, Cecilia M. Pratt, Cameron J. Jui, Nathan T. Blakey, Simon B. Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines |
title | Defluoroalkylation
of Trifluoromethylarenes with Hydrazones:
Rapid Access to Benzylic Difluoroarylethylamines |
title_full | Defluoroalkylation
of Trifluoromethylarenes with Hydrazones:
Rapid Access to Benzylic Difluoroarylethylamines |
title_fullStr | Defluoroalkylation
of Trifluoromethylarenes with Hydrazones:
Rapid Access to Benzylic Difluoroarylethylamines |
title_full_unstemmed | Defluoroalkylation
of Trifluoromethylarenes with Hydrazones:
Rapid Access to Benzylic Difluoroarylethylamines |
title_short | Defluoroalkylation
of Trifluoromethylarenes with Hydrazones:
Rapid Access to Benzylic Difluoroarylethylamines |
title_sort | defluoroalkylation
of trifluoromethylarenes with hydrazones:
rapid access to benzylic difluoroarylethylamines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012270/ https://www.ncbi.nlm.nih.gov/pubmed/36848497 http://dx.doi.org/10.1021/acs.orglett.3c00126 |
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