Boosting the activity of Mizoroki–Heck cross-coupling reactions with a supramolecular palladium catalyst favouring remote Zn⋯pyridine interactions
| Autor: | Naba Abuhafez, Rafael Gramage-Doria |
|---|---|
| Přispěvatelé: | Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-19-CE07-0039,REMOTCAT,Fonctionalisation 'remote' des molecules par catalyse supramoleculaire(2019) |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Faraday Discussions Faraday Discussions, 2023, ⟨10.1039/D2FD00165A⟩ |
| ISSN: | 1364-5498 1359-6640 |
| DOI: | 10.1039/d2fd00165a |
| Popis: | International audience; Transition metal catalysis benefitting from supramolecular interactions in the secondary coordination sphere in order to pre-organize substrates around the active site and reach a specific selectivity typically occur under long reaction times and mild reaction temperatures with the aim to maximize such subtle effects. Herein, we demonstrate that the kinetically labile Zn···N interaction between a pyridine substrate and a zinc-porphyrin site serving for substrate binding is a unique type of non-covalent interaction that enables to identify supramolecular effects in transition metal catalysis after one hour at a high reaction temperature of 130 oC. Under carefully selected reaction conditions, supramolecularly-regulated palladium-catalyzed Mizoroki-Heck reactions between 3-bromopyridine and terminal olefins (acrylates or styrenes) proceeded in a more efficient manner compared to the non-supramolecular version. The supramolecular catalysis developed here displayed also interesting substrate-selectivity patterns. |
| Databáze: | OpenAIRE |
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