Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides

[Image: see text] A new method for the decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with aryl iodides is presented. In contrast to previous studies that form alkyl radicals from carboxylic acid derivatives, no photocatalyst, light, or arylmetal reagent is needed, only n...

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Autores principales: Huihui, Kierra M. M., Caputo, Jill A., Melchor, Zulema, Olivares, Astrid M., Spiewak, Amanda M., Johnson, Keywan A., DiBenedetto, Tarah A., Kim, Seoyoung, Ackerman, Laura K. G., Weix, Daniel J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4841236/
https://www.ncbi.nlm.nih.gov/pubmed/27029833
http://dx.doi.org/10.1021/jacs.6b01533
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author Huihui, Kierra M. M.
Caputo, Jill A.
Melchor, Zulema
Olivares, Astrid M.
Spiewak, Amanda M.
Johnson, Keywan A.
DiBenedetto, Tarah A.
Kim, Seoyoung
Ackerman, Laura K. G.
Weix, Daniel J.
author_facet Huihui, Kierra M. M.
Caputo, Jill A.
Melchor, Zulema
Olivares, Astrid M.
Spiewak, Amanda M.
Johnson, Keywan A.
DiBenedetto, Tarah A.
Kim, Seoyoung
Ackerman, Laura K. G.
Weix, Daniel J.
author_sort Huihui, Kierra M. M.
collection PubMed
description [Image: see text] A new method for the decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with aryl iodides is presented. In contrast to previous studies that form alkyl radicals from carboxylic acid derivatives, no photocatalyst, light, or arylmetal reagent is needed, only nickel and a reducing agent (Zn). Methyl, primary, and secondary alkyl groups can all be coupled in good yield (77% ave yield). One coupling with an acid chloride is also presented. Stoichiometric reactions of (dtbbpy)Ni(2-tolyl)I with an NHP ester show for the first time that arylnickel(II) complexes can directly react with NHP esters to form alkylated arenes.
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spelling pubmed-48412362017-03-30 Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides Huihui, Kierra M. M. Caputo, Jill A. Melchor, Zulema Olivares, Astrid M. Spiewak, Amanda M. Johnson, Keywan A. DiBenedetto, Tarah A. Kim, Seoyoung Ackerman, Laura K. G. Weix, Daniel J. J Am Chem Soc [Image: see text] A new method for the decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with aryl iodides is presented. In contrast to previous studies that form alkyl radicals from carboxylic acid derivatives, no photocatalyst, light, or arylmetal reagent is needed, only nickel and a reducing agent (Zn). Methyl, primary, and secondary alkyl groups can all be coupled in good yield (77% ave yield). One coupling with an acid chloride is also presented. Stoichiometric reactions of (dtbbpy)Ni(2-tolyl)I with an NHP ester show for the first time that arylnickel(II) complexes can directly react with NHP esters to form alkylated arenes. American Chemical Society 2016-03-30 2016-04-20 /pmc/articles/PMC4841236/ /pubmed/27029833 http://dx.doi.org/10.1021/jacs.6b01533 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Huihui, Kierra M. M.
Caputo, Jill A.
Melchor, Zulema
Olivares, Astrid M.
Spiewak, Amanda M.
Johnson, Keywan A.
DiBenedetto, Tarah A.
Kim, Seoyoung
Ackerman, Laura K. G.
Weix, Daniel J.
Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
title Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
title_full Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
title_fullStr Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
title_full_unstemmed Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
title_short Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
title_sort decarboxylative cross-electrophile coupling of n-hydroxyphthalimide esters with aryl iodides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4841236/
https://www.ncbi.nlm.nih.gov/pubmed/27029833
http://dx.doi.org/10.1021/jacs.6b01533
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