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Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend
The identification of a green, versatile, user‐friendly, and efficient methodology is necessary to facilitate the use of Heck‐Cassar‐Sonogashira (HCS) cross‐coupling reaction in drug discovery and industrial production in the pharmaceutical segment. The Heck‐Cassar and Sonogashira protocols, using N...
Autores principales: | , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251985/ https://www.ncbi.nlm.nih.gov/pubmed/33905170 http://dx.doi.org/10.1002/cssc.202100623 |
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author | Fantoni, Tommaso Bernardoni, Sara Mattellone, Alexia Martelli, Giulia Ferrazzano, Lucia Cantelmi, Paolo Corbisiero, Dario Tolomelli, Alessandra Cabri, Walter Vacondio, Federica Ferlenghi, Francesca Mor, Marco Ricci, Antonio |
author_facet | Fantoni, Tommaso Bernardoni, Sara Mattellone, Alexia Martelli, Giulia Ferrazzano, Lucia Cantelmi, Paolo Corbisiero, Dario Tolomelli, Alessandra Cabri, Walter Vacondio, Federica Ferlenghi, Francesca Mor, Marco Ricci, Antonio |
author_sort | Fantoni, Tommaso |
collection | PubMed |
description | The identification of a green, versatile, user‐friendly, and efficient methodology is necessary to facilitate the use of Heck‐Cassar‐Sonogashira (HCS) cross‐coupling reaction in drug discovery and industrial production in the pharmaceutical segment. The Heck‐Cassar and Sonogashira protocols, using N‐hydroxyethylpyrrolidone (HEP)/water/N,N,N′,N′‐tetramethyl guanidine (TMG) as green solvent/base mixture and sulfonated phosphine ligands, allowed to recycle the catalyst, always guaranteeing high yields and fast conversion under mild conditions, with aryl iodides, bromides, and triflates. No catalyst leakage or metal contamination of the final product were observed during the HCS recycling. To our knowledge, a turnover number (TON) up to 2375, a turnover frequency (TOF) of 158 h(−1), and a process mass intensity (PMI) around 7 that decreased around 3 after solvent, base, and palladium recovery, represent one of the best results to date using a sustainable protocol. The Heck‐Cassar protocol using sSPhos was successfully applied to the telescoped synthesis of Erlotinib (TON: 1380; TOF: 46 h(−1)). |
format | Online Article Text |
id | pubmed-8251985 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-82519852021-07-07 Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend Fantoni, Tommaso Bernardoni, Sara Mattellone, Alexia Martelli, Giulia Ferrazzano, Lucia Cantelmi, Paolo Corbisiero, Dario Tolomelli, Alessandra Cabri, Walter Vacondio, Federica Ferlenghi, Francesca Mor, Marco Ricci, Antonio ChemSusChem Full Papers The identification of a green, versatile, user‐friendly, and efficient methodology is necessary to facilitate the use of Heck‐Cassar‐Sonogashira (HCS) cross‐coupling reaction in drug discovery and industrial production in the pharmaceutical segment. The Heck‐Cassar and Sonogashira protocols, using N‐hydroxyethylpyrrolidone (HEP)/water/N,N,N′,N′‐tetramethyl guanidine (TMG) as green solvent/base mixture and sulfonated phosphine ligands, allowed to recycle the catalyst, always guaranteeing high yields and fast conversion under mild conditions, with aryl iodides, bromides, and triflates. No catalyst leakage or metal contamination of the final product were observed during the HCS recycling. To our knowledge, a turnover number (TON) up to 2375, a turnover frequency (TOF) of 158 h(−1), and a process mass intensity (PMI) around 7 that decreased around 3 after solvent, base, and palladium recovery, represent one of the best results to date using a sustainable protocol. The Heck‐Cassar protocol using sSPhos was successfully applied to the telescoped synthesis of Erlotinib (TON: 1380; TOF: 46 h(−1)). John Wiley and Sons Inc. 2021-05-11 2021-06-21 /pmc/articles/PMC8251985/ /pubmed/33905170 http://dx.doi.org/10.1002/cssc.202100623 Text en © 2021 The Authors. ChemSusChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://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 | Full Papers Fantoni, Tommaso Bernardoni, Sara Mattellone, Alexia Martelli, Giulia Ferrazzano, Lucia Cantelmi, Paolo Corbisiero, Dario Tolomelli, Alessandra Cabri, Walter Vacondio, Federica Ferlenghi, Francesca Mor, Marco Ricci, Antonio Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend |
title | Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend |
title_full | Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend |
title_fullStr | Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend |
title_full_unstemmed | Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend |
title_short | Palladium Catalyst Recycling for Heck‐Cassar‐Sonogashira Cross‐Coupling Reactions in Green Solvent/Base Blend |
title_sort | palladium catalyst recycling for heck‐cassar‐sonogashira cross‐coupling reactions in green solvent/base blend |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251985/ https://www.ncbi.nlm.nih.gov/pubmed/33905170 http://dx.doi.org/10.1002/cssc.202100623 |
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