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Pd-Catalyzed α-Arylation of Trimethylsilyl Enolates of α,α-Difluoroacetamides
[Image: see text] We report the arylation and heteroarylation of α,α-difluoro-α-(trimethylsilyl)acetamides with aryl and heteroaryl bromides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)(2)Cy as ligand. A broad range of electronically varied aryl and heteroaryl br...
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/PMC4210146/ https://www.ncbi.nlm.nih.gov/pubmed/25254966 http://dx.doi.org/10.1021/ja508590k |
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author | Ge, Shaozhong Arlow, Sophie I. Mormino, Michael G. Hartwig, John F. |
author_facet | Ge, Shaozhong Arlow, Sophie I. Mormino, Michael G. Hartwig, John F. |
author_sort | Ge, Shaozhong |
collection | PubMed |
description | [Image: see text] We report the arylation and heteroarylation of α,α-difluoro-α-(trimethylsilyl)acetamides with aryl and heteroaryl bromides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)(2)Cy as ligand. A broad range of electronically varied aryl and heteroaryl bromides underwent this transformation to afford α-aryl-α,α-difluoroacetamides in high yields. Due to the electrophilicity of the fluorinated amide, this palladium-catalyzed cross-coupling reaction provides a versatile platform to generate a range of α,α-difluoro carbonyl compounds, such as α-aryl-α,α-difluoroketones, -acetaldehydes, -acetates, and acetic acids, and difluoroalkyl derivatives, such as 2-aryl-2,2-difluoroethanols and -ethylamines, under mild conditions. |
format | Online Article Text |
id | pubmed-4210146 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-42101462015-09-25 Pd-Catalyzed α-Arylation of Trimethylsilyl Enolates of α,α-Difluoroacetamides Ge, Shaozhong Arlow, Sophie I. Mormino, Michael G. Hartwig, John F. J Am Chem Soc [Image: see text] We report the arylation and heteroarylation of α,α-difluoro-α-(trimethylsilyl)acetamides with aryl and heteroaryl bromides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)(2)Cy as ligand. A broad range of electronically varied aryl and heteroaryl bromides underwent this transformation to afford α-aryl-α,α-difluoroacetamides in high yields. Due to the electrophilicity of the fluorinated amide, this palladium-catalyzed cross-coupling reaction provides a versatile platform to generate a range of α,α-difluoro carbonyl compounds, such as α-aryl-α,α-difluoroketones, -acetaldehydes, -acetates, and acetic acids, and difluoroalkyl derivatives, such as 2-aryl-2,2-difluoroethanols and -ethylamines, under mild conditions. American Chemical Society 2014-09-25 2014-10-15 /pmc/articles/PMC4210146/ /pubmed/25254966 http://dx.doi.org/10.1021/ja508590k Text en Copyright © 2014 American Chemical Society |
spellingShingle | Ge, Shaozhong Arlow, Sophie I. Mormino, Michael G. Hartwig, John F. Pd-Catalyzed α-Arylation of Trimethylsilyl Enolates of α,α-Difluoroacetamides |
title | Pd-Catalyzed
α-Arylation of Trimethylsilyl
Enolates of α,α-Difluoroacetamides |
title_full | Pd-Catalyzed
α-Arylation of Trimethylsilyl
Enolates of α,α-Difluoroacetamides |
title_fullStr | Pd-Catalyzed
α-Arylation of Trimethylsilyl
Enolates of α,α-Difluoroacetamides |
title_full_unstemmed | Pd-Catalyzed
α-Arylation of Trimethylsilyl
Enolates of α,α-Difluoroacetamides |
title_short | Pd-Catalyzed
α-Arylation of Trimethylsilyl
Enolates of α,α-Difluoroacetamides |
title_sort | pd-catalyzed
α-arylation of trimethylsilyl
enolates of α,α-difluoroacetamides |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4210146/ https://www.ncbi.nlm.nih.gov/pubmed/25254966 http://dx.doi.org/10.1021/ja508590k |
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