Factors Controlling the Aluminum(I)‐ meta ‐Selective C−H Activation in Arenes

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Cabrera Trujillo, Jorge Juan and Fernández López, Israel (2021) Factors Controlling the Aluminum(I)‐ meta ‐Selective C−H Activation in Arenes. Chemistry – A European Journal, 27 (48). pp. 12422-12429. ISSN 0947-6539

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Official URL: https://doi.org/10.1002/chem.202101944



Abstract

The so far poorly understood factors controlling the complete meta-selectivity observed in the C H activation reactions of alkylarenes promoted by aluminyl anions have been explored in detail by means of Density Functional Theory calculations. To this end, a combination of state-ofthe-art computational methods, namely the activation strain model of reactivity and energy decomposition analysis, has been applied to quantitatively unveil the origin of the selectivity of the transformation as well as the influence of the associated potassium cation. It is found that the selectivity takes place during the initial nucleophilic addition step where the key LP(Al)!π*(C=C) molecular orbital interaction is more stabilizing for the meta-pathway, which results in a stronger interaction between the reactants along the entire transformation.


Item Type:Article
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CRUE-CSIC (Acuerdos Transformativos 2021)

Uncontrolled Keywords:activation strain, aluminum, bond activation, density functional theory calculations, selectivity
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:70133
Deposited On:07 Feb 2022 10:45
Last Modified:22 Feb 2022 09:58

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