Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ

Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ

Ascorbic acid (vitamin C) has been used as a radical initiator in a metal-free direct CH arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitamin C to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation.

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Bibliographic Details
Main Authors: Pinacho Crisóstomo, Fernando R., Martín, Tomás, Carrillo Fumero, Romen
Other Authors: European Commission
Format: artículo biblioteca
Published: Wiley-VCH 2014-02-17
Subjects:Metal‐free reactions, Ascorbic acid, Aromatic substitution, C-H arylation, Green chemistry,
Online Access:http://hdl.handle.net/10261/179833
http://dx.doi.org/10.13039/501100003339
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100003329
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spelling dig-ipna-es-10261-1798332020-12-09T17:43:05Z Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ Pinacho Crisóstomo, Fernando R. Martín, Tomás Carrillo Fumero, Romen European Commission Ministerio de Economía y Competitividad (España) Consejo Superior de Investigaciones Científicas (España) Metal‐free reactions Ascorbic acid Aromatic substitution C-H arylation Green chemistry Ascorbic acid (vitamin C) has been used as a radical initiator in a metal-free direct CH arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitamin C to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation. This research was supported by the Spanish MINECO, cofinanced by the European Regional Development Fund (ERDF) (CTQ2011‐22653). F.P.C. thanks the CSIC for a JAE postdoctoral contract, cofinanced by the FSE. Peer Reviewed 2019-04-10T11:53:19Z 2019-04-10T11:53:19Z 2014-02-17 2019-04-10T11:53:19Z artículo http://purl.org/coar/resource_type/c_6501 doi: 10.1002/anie.201309761 issn: 1433-7851 e-issn: 1521-3773 Angewandte Chemie - International Edition 53(8): 2181-2185 (2014) http://hdl.handle.net/10261/179833 10.1002/anie.201309761 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 https://doi.org/10.1002/anie.201309761 Sí none Wiley-VCH
institution IPNA ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-ipna-es
tag biblioteca
region Europa del Sur
libraryname Biblioteca del IPNA España
topic Metal‐free reactions
Ascorbic acid
Aromatic substitution
C-H arylation
Green chemistry
Metal‐free reactions
Ascorbic acid
Aromatic substitution
C-H arylation
Green chemistry
spellingShingle Metal‐free reactions
Ascorbic acid
Aromatic substitution
C-H arylation
Green chemistry
Metal‐free reactions
Ascorbic acid
Aromatic substitution
C-H arylation
Green chemistry
Pinacho Crisóstomo, Fernando R.
Martín, Tomás
Carrillo Fumero, Romen
Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
description Ascorbic acid (vitamin C) has been used as a radical initiator in a metal-free direct CH arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitamin C to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation.
author2 European Commission
author_facet European Commission
Pinacho Crisóstomo, Fernando R.
Martín, Tomás
Carrillo Fumero, Romen
format artículo
topic_facet Metal‐free reactions
Ascorbic acid
Aromatic substitution
C-H arylation
Green chemistry
author Pinacho Crisóstomo, Fernando R.
Martín, Tomás
Carrillo Fumero, Romen
author_sort Pinacho Crisóstomo, Fernando R.
title Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
title_short Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
title_full Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
title_fullStr Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
title_full_unstemmed Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
title_sort ascorbic acid as an initiator for the direct c-h arylation of (hetero)arenes with anilines nitrosated in situ
publisher Wiley-VCH
publishDate 2014-02-17
url http://hdl.handle.net/10261/179833
http://dx.doi.org/10.13039/501100003339
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100003329
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AT carrillofumeroromen ascorbicacidasaninitiatorforthedirectcharylationofheteroareneswithanilinesnitrosatedinsitu
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