Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents

[Image: see text] The complete regioselective incorporation of carbene units to nonactivated arene rings has been achieved employing gold(I) catalysts bearing alkoxydiaminophosphine ligands, with readily available, nonelaborated ethyl 2-phenyldiazoacetate as the carbene source. These results are in...

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Autores principales: Pizarro, Juan Diego, Schmidtke, Inga L., Nova, Ainara, Fructos, Manuel R., Pérez, Pedro J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9210454/
https://www.ncbi.nlm.nih.gov/pubmed/35756859
http://dx.doi.org/10.1021/acscatal.2c01713
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author Pizarro, Juan Diego
Schmidtke, Inga L.
Nova, Ainara
Fructos, Manuel R.
Pérez, Pedro J.
author_facet Pizarro, Juan Diego
Schmidtke, Inga L.
Nova, Ainara
Fructos, Manuel R.
Pérez, Pedro J.
author_sort Pizarro, Juan Diego
collection PubMed
description [Image: see text] The complete regioselective incorporation of carbene units to nonactivated arene rings has been achieved employing gold(I) catalysts bearing alkoxydiaminophosphine ligands, with readily available, nonelaborated ethyl 2-phenyldiazoacetate as the carbene source. These results are in contrast with the scarce precedents which required highly elaborated diazo substrates. Density functional theory (DFT) calculations have revealed the important role of the R group in the C(R)CO(2)Et fragment, which dramatically affects the energy profile of this transformation.
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spelling pubmed-92104542022-06-22 Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents Pizarro, Juan Diego Schmidtke, Inga L. Nova, Ainara Fructos, Manuel R. Pérez, Pedro J. ACS Catal [Image: see text] The complete regioselective incorporation of carbene units to nonactivated arene rings has been achieved employing gold(I) catalysts bearing alkoxydiaminophosphine ligands, with readily available, nonelaborated ethyl 2-phenyldiazoacetate as the carbene source. These results are in contrast with the scarce precedents which required highly elaborated diazo substrates. Density functional theory (DFT) calculations have revealed the important role of the R group in the C(R)CO(2)Et fragment, which dramatically affects the energy profile of this transformation. American Chemical Society 2022-05-25 2022-06-17 /pmc/articles/PMC9210454/ /pubmed/35756859 http://dx.doi.org/10.1021/acscatal.2c01713 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Pizarro, Juan Diego
Schmidtke, Inga L.
Nova, Ainara
Fructos, Manuel R.
Pérez, Pedro J.
Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents
title Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents
title_full Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents
title_fullStr Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents
title_full_unstemmed Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents
title_short Selective Functionalization of Arene C(sp(2))–H Bonds by Gold Catalysis: The Role of Carbene Substituents
title_sort selective functionalization of arene c(sp(2))–h bonds by gold catalysis: the role of carbene substituents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9210454/
https://www.ncbi.nlm.nih.gov/pubmed/35756859
http://dx.doi.org/10.1021/acscatal.2c01713
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