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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...

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Autores principales: Hendy, Cecilia M., Pratt, Cameron J., Jui, Nathan T., Blakey, Simon B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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