Rhodium-catalysed ortho-alkynylation of nitroarenes

The ortho-alkynylation of nitro-(hetero)arenes takes place in the presence of a Rh(iii) catalyst to deliver a wide variety of alkynylated nitroarenes regioselectively. These interesting products could be further derivatized by selective reduction of the nitro group or palladium-catalysed couplings....

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Detalles Bibliográficos
Autores principales: Tan, Eric, Montesinos-Magraner, Marc, García-Morales, Cristina, Mayans, Joan Guillem, Echavarren, Antonio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8597868/
https://www.ncbi.nlm.nih.gov/pubmed/34820088
http://dx.doi.org/10.1039/d1sc04527j
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author Tan, Eric
Montesinos-Magraner, Marc
García-Morales, Cristina
Mayans, Joan Guillem
Echavarren, Antonio M.
author_facet Tan, Eric
Montesinos-Magraner, Marc
García-Morales, Cristina
Mayans, Joan Guillem
Echavarren, Antonio M.
author_sort Tan, Eric
collection PubMed
description The ortho-alkynylation of nitro-(hetero)arenes takes place in the presence of a Rh(iii) catalyst to deliver a wide variety of alkynylated nitroarenes regioselectively. These interesting products could be further derivatized by selective reduction of the nitro group or palladium-catalysed couplings. Experimental and computational mechanistic studies demonstrate that the reaction proceeds via a turnover-limiting electrophilic C–H metalation ortho to the strongly electron-withdrawing nitro group.
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spelling pubmed-85978682021-11-23 Rhodium-catalysed ortho-alkynylation of nitroarenes Tan, Eric Montesinos-Magraner, Marc García-Morales, Cristina Mayans, Joan Guillem Echavarren, Antonio M. Chem Sci Chemistry The ortho-alkynylation of nitro-(hetero)arenes takes place in the presence of a Rh(iii) catalyst to deliver a wide variety of alkynylated nitroarenes regioselectively. These interesting products could be further derivatized by selective reduction of the nitro group or palladium-catalysed couplings. Experimental and computational mechanistic studies demonstrate that the reaction proceeds via a turnover-limiting electrophilic C–H metalation ortho to the strongly electron-withdrawing nitro group. The Royal Society of Chemistry 2021-10-11 /pmc/articles/PMC8597868/ /pubmed/34820088 http://dx.doi.org/10.1039/d1sc04527j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Tan, Eric
Montesinos-Magraner, Marc
García-Morales, Cristina
Mayans, Joan Guillem
Echavarren, Antonio M.
Rhodium-catalysed ortho-alkynylation of nitroarenes
title Rhodium-catalysed ortho-alkynylation of nitroarenes
title_full Rhodium-catalysed ortho-alkynylation of nitroarenes
title_fullStr Rhodium-catalysed ortho-alkynylation of nitroarenes
title_full_unstemmed Rhodium-catalysed ortho-alkynylation of nitroarenes
title_short Rhodium-catalysed ortho-alkynylation of nitroarenes
title_sort rhodium-catalysed ortho-alkynylation of nitroarenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8597868/
https://www.ncbi.nlm.nih.gov/pubmed/34820088
http://dx.doi.org/10.1039/d1sc04527j
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AT mayansjoanguillem rhodiumcatalysedorthoalkynylationofnitroarenes
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