A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes

[Image: see text] A simple method for direct C–H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reacti...

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Autores principales: Foo, Klement, Sella, Eran, Thomé, Isabelle, Eastgate, Martin D., Baran, Phil S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4210156/
https://www.ncbi.nlm.nih.gov/pubmed/24654983
http://dx.doi.org/10.1021/ja501879c
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author Foo, Klement
Sella, Eran
Thomé, Isabelle
Eastgate, Martin D.
Baran, Phil S.
author_facet Foo, Klement
Sella, Eran
Thomé, Isabelle
Eastgate, Martin D.
Baran, Phil S.
author_sort Foo, Klement
collection PubMed
description [Image: see text] A simple method for direct C–H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reaction is broad, the conditions are extremely mild, and the reaction is tolerant of oxidizable and acid-labile functionality, multiple heteroatoms, and aryl iodides. Mechanistic studies indicate that ferrocene (Cp(2)Fe) plays the role of an electron shuttle in the decomposition of the perester reagent, delivering a succinimidyl radical ready to add to an aromatic system.
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spelling pubmed-42101562015-03-23 A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes Foo, Klement Sella, Eran Thomé, Isabelle Eastgate, Martin D. Baran, Phil S. J Am Chem Soc [Image: see text] A simple method for direct C–H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reaction is broad, the conditions are extremely mild, and the reaction is tolerant of oxidizable and acid-labile functionality, multiple heteroatoms, and aryl iodides. Mechanistic studies indicate that ferrocene (Cp(2)Fe) plays the role of an electron shuttle in the decomposition of the perester reagent, delivering a succinimidyl radical ready to add to an aromatic system. American Chemical Society 2014-03-23 2014-04-09 /pmc/articles/PMC4210156/ /pubmed/24654983 http://dx.doi.org/10.1021/ja501879c Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Foo, Klement
Sella, Eran
Thomé, Isabelle
Eastgate, Martin D.
Baran, Phil S.
A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
title A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
title_full A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
title_fullStr A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
title_full_unstemmed A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
title_short A Mild, Ferrocene-Catalyzed C–H Imidation of (Hetero)Arenes
title_sort mild, ferrocene-catalyzed c–h imidation of (hetero)arenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4210156/
https://www.ncbi.nlm.nih.gov/pubmed/24654983
http://dx.doi.org/10.1021/ja501879c
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