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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...

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Autores principales: Ge, Shaozhong, Arlow, Sophie I., Mormino, Michael G., Hartwig, John F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
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.
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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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