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Relative Strength of Common Directing Groups in Palladium-Catalyzed Aromatic C-H Activation
AstraZeneca Gothenburg, Hit Discovery, Discovery Sci R&D, S-43183 Molndal, Sweden.
AstraZeneca Gothenburg, Med Chem Res & Early Dev, Cardiovasc Renal & Metab, BioPharmaceut R&D, S-43183 Molndal, Sweden.
AstraZeneca Gothenburg, Med Chem Res & Early Dev, Cardiovasc Renal & Metab, BioPharmaceut R&D, S-43183 Molndal, Sweden.
AstraZeneca Gothenburg, BioPharmaceut R&D, Resp, S-43183 Molndal, Sweden.
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2019 (English)In: ISCIENCE, ISSN 2589-0042, Vol. 20, p. 373-+Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
CELL PRESS , 2019. Vol. 20, p. 373-+
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Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-397315DOI: 10.1016/j.isci.2019.09.035ISI: 000493388000029PubMedID: 31614320OAI: oai:DiVA.org:uu-397315DiVA, id: diva2:1372727
Available from: 2019-11-25 Created: 2019-11-25 Last updated: 2019-11-25Bibliographically approved

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