A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions. Lu, J., Donnecke, S., Paci, I., & Leitch, D. C. Chemical Science, 2022. ![A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions [link]](https://bibbase.org/img/filetypes/link.svg "link")
Paper doi abstract bibtex We report a quantitative model for oxidative addition reactivity in palladium-catalyzed cross-coupling, which is broadly applicable to predict reactivity and selectivity for complex substrates from simple molecular descriptors. , Making accurate, quantitative predictions of chemical reactivity based on molecular structure is an unsolved problem in chemical synthesis, particularly for complex molecules. We report an approach to reactivity prediction for catalytic reactions based on quantitative structure-reactivity models for a key step common to many catalytic mechanisms. We demonstrate this approach with a mechanistically based model for the oxidative addition of (hetero)aryl electrophiles to palladium(0), which is a key step in myriad catalytic processes. This model links simple molecular descriptors to relative rates of oxidative addition for 79 substrates, including chloride, bromide and triflate leaving groups. Because oxidative addition often controls the rate and/or selectivity of palladium-catalyzed reactions, this model can be used to make quantitative predictions about catalytic reaction outcomes. Demonstrated applications include a multivariate linear model for the initial rate of Sonogashira coupling reactions, and successful site-selectivity predictions for Suzuki, Buchwald-Hartwig, and Stille reactions of multihalogenated substrates relevant to the synthesis of pharmaceuticals and natural products.
@article{lu_reactivity_2022,
title = {A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions},
issn = {2041-6520, 2041-6539},
url = {http://xlink.rsc.org/?DOI=D2SC00174H},
doi = {10.1039/D2SC00174H},
abstract = {We report a quantitative model for oxidative addition reactivity in palladium-catalyzed cross-coupling, which is broadly applicable to predict reactivity and selectivity for complex substrates from simple molecular descriptors.
,
Making accurate, quantitative predictions of chemical reactivity based on molecular structure is an unsolved problem in chemical synthesis, particularly for complex molecules. We report an approach to reactivity prediction for catalytic reactions based on quantitative structure-reactivity models for a key step common to many catalytic mechanisms. We demonstrate this approach with a mechanistically based model for the oxidative addition of (hetero)aryl electrophiles to palladium(0), which is a key step in myriad catalytic processes. This model links simple molecular descriptors to relative rates of oxidative addition for 79 substrates, including chloride, bromide and triflate leaving groups. Because oxidative addition often controls the rate and/or selectivity of palladium-catalyzed reactions, this model can be used to make quantitative predictions about catalytic reaction outcomes. Demonstrated applications include a multivariate linear model for the initial rate of Sonogashira coupling reactions, and successful site-selectivity predictions for Suzuki, Buchwald-Hartwig, and Stille reactions of multihalogenated substrates relevant to the synthesis of pharmaceuticals and natural products.},
language = {en},
urldate = {2022-03-07},
journal = {Chemical Science},
author = {Lu, Jingru and Donnecke, Sofia and Paci, Irina and Leitch, David C.},
year = {2022},
pages = {10.1039.D2SC00174H},
}
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We report an approach to reactivity prediction for catalytic reactions based on quantitative structure-reactivity models for a key step common to many catalytic mechanisms. We demonstrate this approach with a mechanistically based model for the oxidative addition of (hetero)aryl electrophiles to palladium(0), which is a key step in myriad catalytic processes. This model links simple molecular descriptors to relative rates of oxidative addition for 79 substrates, including chloride, bromide and triflate leaving groups. Because oxidative addition often controls the rate and/or selectivity of palladium-catalyzed reactions, this model can be used to make quantitative predictions about catalytic reaction outcomes. Demonstrated applications include a multivariate linear model for the initial rate of Sonogashira coupling reactions, and successful site-selectivity predictions for Suzuki, Buchwald-Hartwig, and Stille reactions of multihalogenated substrates relevant to the synthesis of pharmaceuticals and natural products.","language":"en","urldate":"2022-03-07","journal":"Chemical Science","author":[{"propositions":[],"lastnames":["Lu"],"firstnames":["Jingru"],"suffixes":[]},{"propositions":[],"lastnames":["Donnecke"],"firstnames":["Sofia"],"suffixes":[]},{"propositions":[],"lastnames":["Paci"],"firstnames":["Irina"],"suffixes":[]},{"propositions":[],"lastnames":["Leitch"],"firstnames":["David","C."],"suffixes":[]}],"year":"2022","pages":"10.1039.D2SC00174H","bibtex":"@article{lu_reactivity_2022,\n\ttitle = {A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions},\n\tissn = {2041-6520, 2041-6539},\n\turl = {http://xlink.rsc.org/?DOI=D2SC00174H},\n\tdoi = {10.1039/D2SC00174H},\n\tabstract = {We report a quantitative model for oxidative addition reactivity in palladium-catalyzed cross-coupling, which is broadly applicable to predict reactivity and selectivity for complex substrates from simple molecular descriptors.\n , \n Making accurate, quantitative predictions of chemical reactivity based on molecular structure is an unsolved problem in chemical synthesis, particularly for complex molecules. 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