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Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction
[Image: see text] Nickel catalysts represent a low cost and environmentally friendly alternative to palladium-based catalytic systems for Suzuki–Miyaura cross-coupling (SMC) reactions. However, nickel catalysts have suffered from poor air, moisture, and thermal stabilities, especially at high cataly...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7513363/ https://www.ncbi.nlm.nih.gov/pubmed/32984724 http://dx.doi.org/10.1021/acsomega.0c03415 |
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author | Talukder, Md Muktadir Cue, John Michael O. Miller, Justin T. Gamage, Prabhath L. Aslam, Amina McCandless, Gregory T. Biewer, Michael C. Stefan, Mihaela C. |
author_facet | Talukder, Md Muktadir Cue, John Michael O. Miller, Justin T. Gamage, Prabhath L. Aslam, Amina McCandless, Gregory T. Biewer, Michael C. Stefan, Mihaela C. |
author_sort | Talukder, Md Muktadir |
collection | PubMed |
description | [Image: see text] Nickel catalysts represent a low cost and environmentally friendly alternative to palladium-based catalytic systems for Suzuki–Miyaura cross-coupling (SMC) reactions. However, nickel catalysts have suffered from poor air, moisture, and thermal stabilities, especially at high catalyst loading, requiring controlled reaction conditions. In this report, we examine a family of mono- and dinuclear Ni(II) and Pd(II) complexes with a diverse and versatile α-diimine ligand environment for SMC reactions. To evaluate the ligand steric effects, including the bite angle in the reaction outcomes, the structural variation of the complexes was achieved by incorporating iminopyridine- and acenaphthene-based ligands. Moreover, the impact of substrate bulkiness was investigated by reacting various aryl bromides with phenylboronic acid, 2-naphthylboronic acid, and 9-phenanthracenylboronic acid. Yields were the best with the dinuclear complex, being nearly quantitative (93–99%), followed by the mononuclear complexes, giving yields of 78–98%. Consequently, α-diimine-based ligands have the potential to deliver Ni-based systems as sustainable catalysts in SMC. |
format | Online Article Text |
id | pubmed-7513363 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-75133632020-09-25 Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction Talukder, Md Muktadir Cue, John Michael O. Miller, Justin T. Gamage, Prabhath L. Aslam, Amina McCandless, Gregory T. Biewer, Michael C. Stefan, Mihaela C. ACS Omega [Image: see text] Nickel catalysts represent a low cost and environmentally friendly alternative to palladium-based catalytic systems for Suzuki–Miyaura cross-coupling (SMC) reactions. However, nickel catalysts have suffered from poor air, moisture, and thermal stabilities, especially at high catalyst loading, requiring controlled reaction conditions. In this report, we examine a family of mono- and dinuclear Ni(II) and Pd(II) complexes with a diverse and versatile α-diimine ligand environment for SMC reactions. To evaluate the ligand steric effects, including the bite angle in the reaction outcomes, the structural variation of the complexes was achieved by incorporating iminopyridine- and acenaphthene-based ligands. Moreover, the impact of substrate bulkiness was investigated by reacting various aryl bromides with phenylboronic acid, 2-naphthylboronic acid, and 9-phenanthracenylboronic acid. Yields were the best with the dinuclear complex, being nearly quantitative (93–99%), followed by the mononuclear complexes, giving yields of 78–98%. Consequently, α-diimine-based ligands have the potential to deliver Ni-based systems as sustainable catalysts in SMC. American Chemical Society 2020-09-10 /pmc/articles/PMC7513363/ /pubmed/32984724 http://dx.doi.org/10.1021/acsomega.0c03415 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Talukder, Md Muktadir Cue, John Michael O. Miller, Justin T. Gamage, Prabhath L. Aslam, Amina McCandless, Gregory T. Biewer, Michael C. Stefan, Mihaela C. Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling Reaction |
title | Ligand Steric Effects of α-Diimine Nickel(II)
and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling
Reaction |
title_full | Ligand Steric Effects of α-Diimine Nickel(II)
and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling
Reaction |
title_fullStr | Ligand Steric Effects of α-Diimine Nickel(II)
and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling
Reaction |
title_full_unstemmed | Ligand Steric Effects of α-Diimine Nickel(II)
and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling
Reaction |
title_short | Ligand Steric Effects of α-Diimine Nickel(II)
and Palladium(II) Complexes in the Suzuki–Miyaura Cross-Coupling
Reaction |
title_sort | ligand steric effects of α-diimine nickel(ii)
and palladium(ii) complexes in the suzuki–miyaura cross-coupling
reaction |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7513363/ https://www.ncbi.nlm.nih.gov/pubmed/32984724 http://dx.doi.org/10.1021/acsomega.0c03415 |
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