Mechanistic Features in Al(I)-Mediated Oxidative Addition of Aryl C-F Bonds: Insights From Density Functional Theory Calculations

Al(I)介导的芳基CF键氧化加成反应的机理特征:来自密度泛函理论计算的启示

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Abstract

The oxidative addition of a range of robust aryl C-F bonds to a single Al(I) center supported by a (NacNac)(-) bidentate ligand ((NacNac)(-) = [ArNC(Me)CHC(Me)NAr](-) and Ar = 2,6- Pr2i C(6)H(3)) have been explored by density functional theory calculations. Our calculations demonstrate that the Al(I) center-mediated C-F insertion generally proceeds via the concerted mechanism that involve both the donation ( nAl → σC-F* ) and back-donation ( σF(p) → πAl(p)* ) interactions. In addition, the predicted free energy barriers for the C-F bond activation show good agreement with the experimental information available. Finally, the comparative studies show that B(I) is the most active among group III metals (B, Al, Ga), thus supplying a testable prediction for experiments.

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