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New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries
Ligands are essential for controlling the reactivity and selectivity of transition metal-catalyzed reactions. Access to large phosphine ligand libraries has become an essential tool for the application of metal-catalyzed reactions industrially, but these existing libraries are not well suited to new...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5123601/ https://www.ncbi.nlm.nih.gov/pubmed/27874864 http://dx.doi.org/10.1038/nchem.2587 |
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author | Hansen, Eric C. Pedro, Dylan J. Wotal, Alexander C. Gower, Nicholas J. Nelson, Jade D. Caron, Stephane Weix, Daniel J. |
author_facet | Hansen, Eric C. Pedro, Dylan J. Wotal, Alexander C. Gower, Nicholas J. Nelson, Jade D. Caron, Stephane Weix, Daniel J. |
author_sort | Hansen, Eric C. |
collection | PubMed |
description | Ligands are essential for controlling the reactivity and selectivity of transition metal-catalyzed reactions. Access to large phosphine ligand libraries has become an essential tool for the application of metal-catalyzed reactions industrially, but these existing libraries are not well suited to new catalytic methods based on non-precious metals (i.e., Ni, Cu, Fe). The development of the requisite nitrogen- and oxygen-based ligand libraries lags far behind phosphines and the development of new libraries is anticipated to be time consuming. Here we show that this process can be dramatically accelerated by mining a typical pharmaceutical compound library that is rich in heterocycles for new ligands. Using this approach, we were able to screen a structurally diverse set of compounds with minimal synthetic effort and identify several new ligand classes for nickel-catalyzed cross-electrophile coupling. These new ligands gave improved yields for challenging cross-couplings of pharmaceutically relevant substrates compared to previously published ligands. |
format | Online Article Text |
id | pubmed-5123601 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
record_format | MEDLINE/PubMed |
spelling | pubmed-51236012017-02-08 New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries Hansen, Eric C. Pedro, Dylan J. Wotal, Alexander C. Gower, Nicholas J. Nelson, Jade D. Caron, Stephane Weix, Daniel J. Nat Chem Article Ligands are essential for controlling the reactivity and selectivity of transition metal-catalyzed reactions. Access to large phosphine ligand libraries has become an essential tool for the application of metal-catalyzed reactions industrially, but these existing libraries are not well suited to new catalytic methods based on non-precious metals (i.e., Ni, Cu, Fe). The development of the requisite nitrogen- and oxygen-based ligand libraries lags far behind phosphines and the development of new libraries is anticipated to be time consuming. Here we show that this process can be dramatically accelerated by mining a typical pharmaceutical compound library that is rich in heterocycles for new ligands. Using this approach, we were able to screen a structurally diverse set of compounds with minimal synthetic effort and identify several new ligand classes for nickel-catalyzed cross-electrophile coupling. These new ligands gave improved yields for challenging cross-couplings of pharmaceutically relevant substrates compared to previously published ligands. 2016-08-08 2016-12 /pmc/articles/PMC5123601/ /pubmed/27874864 http://dx.doi.org/10.1038/nchem.2587 Text en Reprints and permissions information is available at www.nature.com/reprints (http://www.nature.com/reprints) . Users may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use:http://www.nature.com/authors/editorial_policies/license.html#terms |
spellingShingle | Article Hansen, Eric C. Pedro, Dylan J. Wotal, Alexander C. Gower, Nicholas J. Nelson, Jade D. Caron, Stephane Weix, Daniel J. New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries |
title | New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries |
title_full | New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries |
title_fullStr | New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries |
title_full_unstemmed | New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries |
title_short | New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries |
title_sort | new ligands for nickel catalysis from diverse pharmaceutical heterocycle libraries |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5123601/ https://www.ncbi.nlm.nih.gov/pubmed/27874864 http://dx.doi.org/10.1038/nchem.2587 |
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