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Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes

A range of arylgold compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos o...

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Autores principales: Richard, Marcia E, Fraccica, Daniel V, Garcia, Kevin J, Miller, Erica J, Ciccarelli, Rosa M, Holahan, Erin C, Resh, Victoria L, Shah, Aakash, Findeis, Peter M, Jr., Robert A Stockland
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817533/
https://www.ncbi.nlm.nih.gov/pubmed/24204410
http://dx.doi.org/10.3762/bjoc.9.235
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author Richard, Marcia E
Fraccica, Daniel V
Garcia, Kevin J
Miller, Erica J
Ciccarelli, Rosa M
Holahan, Erin C
Resh, Victoria L
Shah, Aakash
Findeis, Peter M
Jr., Robert A Stockland
author_facet Richard, Marcia E
Fraccica, Daniel V
Garcia, Kevin J
Miller, Erica J
Ciccarelli, Rosa M
Holahan, Erin C
Resh, Victoria L
Shah, Aakash
Findeis, Peter M
Jr., Robert A Stockland
author_sort Richard, Marcia E
collection PubMed
description A range of arylgold compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos or IPr/SIPr. Phenols bearing either electron-withdrawing or electron-donating groups were efficiently added using these catalysts. No silver salts, acids, or solvents were needed for the catalysis, and either microwave or conventional heating afforded moderate to excellent yields of the vinyl ethers.
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spelling pubmed-38175332013-11-07 Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes Richard, Marcia E Fraccica, Daniel V Garcia, Kevin J Miller, Erica J Ciccarelli, Rosa M Holahan, Erin C Resh, Victoria L Shah, Aakash Findeis, Peter M Jr., Robert A Stockland Beilstein J Org Chem Full Research Paper A range of arylgold compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos or IPr/SIPr. Phenols bearing either electron-withdrawing or electron-donating groups were efficiently added using these catalysts. No silver salts, acids, or solvents were needed for the catalysis, and either microwave or conventional heating afforded moderate to excellent yields of the vinyl ethers. Beilstein-Institut 2013-10-02 /pmc/articles/PMC3817533/ /pubmed/24204410 http://dx.doi.org/10.3762/bjoc.9.235 Text en Copyright © 2013, Richard et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Richard, Marcia E
Fraccica, Daniel V
Garcia, Kevin J
Miller, Erica J
Ciccarelli, Rosa M
Holahan, Erin C
Resh, Victoria L
Shah, Aakash
Findeis, Peter M
Jr., Robert A Stockland
Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
title Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
title_full Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
title_fullStr Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
title_full_unstemmed Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
title_short Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
title_sort acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817533/
https://www.ncbi.nlm.nih.gov/pubmed/24204410
http://dx.doi.org/10.3762/bjoc.9.235
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