Parameterization of phosphine ligands reveals mechanistic pathways and predicts reaction outcomes
| Autor: | Anat Milo, David P. Hickey, Zachary L. Niemeyer, Matthew S. Sigman |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Reaction mechanism
Future studies 010405 organic chemistry Chemistry Ligand General Chemical Engineering Site selectivity General Chemistry 010402 general chemistry 01 natural sciences Oxidative addition 0104 chemical sciences chemistry.chemical_compound Suzuki reaction Computational chemistry Phosphine |
| Zdroj: | Nature Chemistry. 8:610-617 |
| ISSN: | 1755-4349 1755-4330 |
| DOI: | 10.1038/nchem.2501 |
| Popis: | The mechanistic foundation behind the identity of a phosphine ligand that best promotes a desired reaction outcome is often non-intuitive, and thus has been addressed in numerous experimental and theoretical studies. In this work, multivariate correlations of reaction outcomes using 38 different phosphine ligands were combined with classic potentiometric analyses to study a Suzuki reaction, for which the site selectivity of oxidative addition is highly dependent on the nature of the phosphine. These studies shed light on the generality of hypotheses regarding the structural influence of different classes of phosphine ligands on the reaction mechanism(s), and deliver a methodology that should prove useful in future studies of phosphine ligands. |
| Databáze: | OpenAIRE |
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