Relative Strength of Common Directing Groups in Palladium-Catalyzed Aromatic C−H Activation
Efficient functionalization of C−H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we des...
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| Published in | iScience Vol. 20; pp. 373 - 391 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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United States
Elsevier Inc
25.10.2019
Elsevier |
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| Abstract | Efficient functionalization of C−H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe a methodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C−H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space.
[Display omitted]
•Directing group strength for ortho-palladation can be predicted quantum chemically•Correlation with fragments allow regioselectivity predictions in complex molecules•Directing strength is enhanced by deprotonation under the reaction conditions•Palladation in between two directing groups is disfavored sterically; no synergy
Catalysis; Computational Molecular Modelling; Organic Reaction |
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| AbstractList | Efficient functionalization of C-H bonds can be achieved using transition metal catalysts, such as Pd(OAc)(2). To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe amethodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C-H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space. Efficient functionalization of C−H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe a methodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C−H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space. : Catalysis; Computational Molecular Modelling; Organic Reaction Subject Areas: Catalysis, Computational Molecular Modelling, Organic Reaction Efficient functionalization of C−H bonds can be achieved using transition metal catalysts, such as Pd(OAc) 2 . To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe a methodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C−H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space. • Directing group strength for ortho- palladation can be predicted quantum chemically • Correlation with fragments allow regioselectivity predictions in complex molecules • Directing strength is enhanced by deprotonation under the reaction conditions • Palladation in between two directing groups is disfavored sterically; no synergy Catalysis; Computational Molecular Modelling; Organic Reaction Efficient functionalization of C-H bonds can be achieved using transition metal catalysts, such as Pd(OAc) . To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe a methodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C-H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space. Efficient functionalization of C-H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe a methodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C-H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space.Efficient functionalization of C-H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe a methodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C-H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space. Efficient functionalization of C−H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these reactions, some functional groups on the substrate may be used as directing groups, guiding the reactivity to an ortho position. Herein, we describe a methodology to score the relative strength of such directing groups in palladium-catalyzed aromatic C−H activation. The results have been collected into a scale that serves to predict the regioselectivity on molecules with multiple competing directing groups. We demonstrate that this scale yields accurate predictions on over a hundred examples, taken from the literature. In addition to the regioselectivity prediction on complex molecules, the knowledge of the relative strengths of directing groups can also be used to work with new combinations of functionalities, exploring uncharted chemical space. [Display omitted] •Directing group strength for ortho-palladation can be predicted quantum chemically•Correlation with fragments allow regioselectivity predictions in complex molecules•Directing strength is enhanced by deprotonation under the reaction conditions•Palladation in between two directing groups is disfavored sterically; no synergy Catalysis; Computational Molecular Modelling; Organic Reaction |
| Author | Johansson, Magnus Jan Terstiege, Ina Norrby, Per-Ola Sköld, Christian Muratore, Michael Éric Tomberg, Anna |
| AuthorAffiliation | 5 Data Science & Modelling, Pharmaceutical Sciences, R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden 3 Respiratory, BioPharmaceuticals R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden 2 Medicinal Chemistry, Research and Early Development Cardiovascular, Renal and Metabolism, BioPharmaceuticals R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden 1 Hit Discovery, Discovery Sciences, R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden 4 Department of Medicinal Chemistry, Drug Design and Development, Uppsala University, Box 574, Uppsala 751 23, Sweden |
| AuthorAffiliation_xml | – name: 3 Respiratory, BioPharmaceuticals R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden – name: 5 Data Science & Modelling, Pharmaceutical Sciences, R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden – name: 1 Hit Discovery, Discovery Sciences, R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden – name: 4 Department of Medicinal Chemistry, Drug Design and Development, Uppsala University, Box 574, Uppsala 751 23, Sweden – name: 2 Medicinal Chemistry, Research and Early Development Cardiovascular, Renal and Metabolism, BioPharmaceuticals R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden |
| Author_xml | – sequence: 1 givenname: Anna surname: Tomberg fullname: Tomberg, Anna organization: Hit Discovery, Discovery Sciences, R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden – sequence: 2 givenname: Michael Éric surname: Muratore fullname: Muratore, Michael Éric organization: Medicinal Chemistry, Research and Early Development Cardiovascular, Renal and Metabolism, BioPharmaceuticals R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden – sequence: 3 givenname: Magnus Jan surname: Johansson fullname: Johansson, Magnus Jan organization: Medicinal Chemistry, Research and Early Development Cardiovascular, Renal and Metabolism, BioPharmaceuticals R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden – sequence: 4 givenname: Ina orcidid: 0000-0003-4087-9710 surname: Terstiege fullname: Terstiege, Ina organization: Respiratory, BioPharmaceuticals R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden – sequence: 5 givenname: Christian surname: Sköld fullname: Sköld, Christian organization: Department of Medicinal Chemistry, Drug Design and Development, Uppsala University, Box 574, Uppsala 751 23, Sweden – sequence: 6 givenname: Per-Ola orcidid: 0000-0002-2419-0705 surname: Norrby fullname: Norrby, Per-Ola email: per-ola.norrby@astrazeneca.com organization: Data Science & Modelling, Pharmaceutical Sciences, R&D, AstraZeneca Gothenburg, Mölndal 431 83, Sweden |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31614320$$D View this record in MEDLINE/PubMed https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-397315$$DView record from Swedish Publication Index |
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| Snippet | Efficient functionalization of C−H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these... Efficient functionalization of C-H bonds can be achieved using transition metal catalysts, such as Pd(OAc) . To better control the regioselectivity in these... Efficient functionalization of C-H bonds can be achieved using transition metal catalysts, such as Pd(OAc)2. To better control the regioselectivity in these... Efficient functionalization of C−H bonds can be achieved using transition metal catalysts, such as Pd(OAc) 2 . To better control the regioselectivity in these... Efficient functionalization of C-H bonds can be achieved using transition metal catalysts, such as Pd(OAc)(2). To better control the regioselectivity in these... |
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| Title | Relative Strength of Common Directing Groups in Palladium-Catalyzed Aromatic C−H Activation |
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