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Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents
Although the use of catalytic rather than stoichiometric amounts of metal mediator in cross-coupling reactions between organic halides and organometallic counterparts improves significantly the atom economy and waste production, the use of solvents and stoichiometric generation of main-group byprodu...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4895725/ https://www.ncbi.nlm.nih.gov/pubmed/27251636 http://dx.doi.org/10.1038/ncomms11698 |
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author | Pinxterhuis, Erik B. Giannerini, Massimo Hornillos, Valentín Feringa, Ben L. |
author_facet | Pinxterhuis, Erik B. Giannerini, Massimo Hornillos, Valentín Feringa, Ben L. |
author_sort | Pinxterhuis, Erik B. |
collection | PubMed |
description | Although the use of catalytic rather than stoichiometric amounts of metal mediator in cross-coupling reactions between organic halides and organometallic counterparts improves significantly the atom economy and waste production, the use of solvents and stoichiometric generation of main-group byproducts (B, Sn and Zn) hamper the ‘greenness' and industrial efficiency of these processes. Here we present a highly selective and green Pd-catalysed cross-coupling between organic halides and organolithium reagents proceeding without additional solvents and with short reaction times (10 min). This method bypasses a number of challenges previously encountered in Pd-catalysed cross-coupling with organolithium compounds such as strict exclusion of moisture, dilution and slow addition. Operational ease of this protocol combines the use of industrially viable catalysts loadings (down to 0.1 mol%), scalability of the process (tested up to 120 mmol) and exceptionally favourable environmental impact (E factors in several cases as low as 1). |
format | Online Article Text |
id | pubmed-4895725 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-48957252016-08-18 Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents Pinxterhuis, Erik B. Giannerini, Massimo Hornillos, Valentín Feringa, Ben L. Nat Commun Article Although the use of catalytic rather than stoichiometric amounts of metal mediator in cross-coupling reactions between organic halides and organometallic counterparts improves significantly the atom economy and waste production, the use of solvents and stoichiometric generation of main-group byproducts (B, Sn and Zn) hamper the ‘greenness' and industrial efficiency of these processes. Here we present a highly selective and green Pd-catalysed cross-coupling between organic halides and organolithium reagents proceeding without additional solvents and with short reaction times (10 min). This method bypasses a number of challenges previously encountered in Pd-catalysed cross-coupling with organolithium compounds such as strict exclusion of moisture, dilution and slow addition. Operational ease of this protocol combines the use of industrially viable catalysts loadings (down to 0.1 mol%), scalability of the process (tested up to 120 mmol) and exceptionally favourable environmental impact (E factors in several cases as low as 1). Nature Publishing Group 2016-06-02 /pmc/articles/PMC4895725/ /pubmed/27251636 http://dx.doi.org/10.1038/ncomms11698 Text en Copyright © 2016, Nature Publishing Group, a division of Macmillan Publishers Limited. All Rights Reserved. http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Article Pinxterhuis, Erik B. Giannerini, Massimo Hornillos, Valentín Feringa, Ben L. Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents |
title | Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents |
title_full | Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents |
title_fullStr | Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents |
title_full_unstemmed | Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents |
title_short | Fast, greener and scalable direct coupling of organolithium compounds with no additional solvents |
title_sort | fast, greener and scalable direct coupling of organolithium compounds with no additional solvents |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4895725/ https://www.ncbi.nlm.nih.gov/pubmed/27251636 http://dx.doi.org/10.1038/ncomms11698 |
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