Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators

[Image: see text] α,β-Unsaturated carboxylic acids undergo Rh(III)-catalyzed decarboxylative coupling with α,β-unsaturated O-pivaloyl oximes to provide substituted pyridines in good yield. The carboxylic acid, which is removed by decarboxylation, serves as a traceless activating group, giving 5-subs...

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Autores principales: Neely, Jamie M., Rovis, Tomislav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985489/
https://www.ncbi.nlm.nih.gov/pubmed/24512241
http://dx.doi.org/10.1021/ja412444d
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author Neely, Jamie M.
Rovis, Tomislav
author_facet Neely, Jamie M.
Rovis, Tomislav
author_sort Neely, Jamie M.
collection PubMed
description [Image: see text] α,β-Unsaturated carboxylic acids undergo Rh(III)-catalyzed decarboxylative coupling with α,β-unsaturated O-pivaloyl oximes to provide substituted pyridines in good yield. The carboxylic acid, which is removed by decarboxylation, serves as a traceless activating group, giving 5-substituted pyridines with very high levels of regioselectivity. Mechanistic studies rule out a picolinic acid intermediate, and an isolable rhodium complex sheds further light on the reaction mechanism.
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spelling pubmed-39854892015-02-10 Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators Neely, Jamie M. Rovis, Tomislav J Am Chem Soc [Image: see text] α,β-Unsaturated carboxylic acids undergo Rh(III)-catalyzed decarboxylative coupling with α,β-unsaturated O-pivaloyl oximes to provide substituted pyridines in good yield. The carboxylic acid, which is removed by decarboxylation, serves as a traceless activating group, giving 5-substituted pyridines with very high levels of regioselectivity. Mechanistic studies rule out a picolinic acid intermediate, and an isolable rhodium complex sheds further light on the reaction mechanism. American Chemical Society 2014-02-10 2014-02-19 /pmc/articles/PMC3985489/ /pubmed/24512241 http://dx.doi.org/10.1021/ja412444d Text en Copyright © 2014 American Chemical Society
spellingShingle Neely, Jamie M.
Rovis, Tomislav
Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
title Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
title_full Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
title_fullStr Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
title_full_unstemmed Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
title_short Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
title_sort rh(iii)-catalyzed decarboxylative coupling of acrylic acids with unsaturated oxime esters: carboxylic acids serve as traceless activators
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985489/
https://www.ncbi.nlm.nih.gov/pubmed/24512241
http://dx.doi.org/10.1021/ja412444d
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AT rovistomislav rhiiicatalyzeddecarboxylativecouplingofacrylicacidswithunsaturatedoximeesterscarboxylicacidsserveastracelessactivators

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