One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts

A transition‐metal‐free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one‐pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has b...

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Detalles Bibliográficos
Autores principales: Reitti, Marcus, Villo, Piret, Olofsson, Berit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5089574/
https://www.ncbi.nlm.nih.gov/pubmed/27272891
http://dx.doi.org/10.1002/anie.201603175
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author Reitti, Marcus
Villo, Piret
Olofsson, Berit
author_facet Reitti, Marcus
Villo, Piret
Olofsson, Berit
author_sort Reitti, Marcus
collection PubMed
description A transition‐metal‐free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one‐pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryliodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.
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spelling pubmed-50895742016-11-09 One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts Reitti, Marcus Villo, Piret Olofsson, Berit Angew Chem Int Ed Engl Communications A transition‐metal‐free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one‐pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryliodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway. John Wiley and Sons Inc. 2016-06-08 2016-07-25 /pmc/articles/PMC5089574/ /pubmed/27272891 http://dx.doi.org/10.1002/anie.201603175 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Reitti, Marcus
Villo, Piret
Olofsson, Berit
One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts
title One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts
title_full One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts
title_fullStr One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts
title_full_unstemmed One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts
title_short One‐Pot C−H Functionalization of Arenes by Diaryliodonium Salts
title_sort one‐pot c−h functionalization of arenes by diaryliodonium salts
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5089574/
https://www.ncbi.nlm.nih.gov/pubmed/27272891
http://dx.doi.org/10.1002/anie.201603175
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