Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Molecular Adsorbates Switch on Heterogeneous Catalysis: Induction of Reactivity by N-Heterocyclic Carbenes

Molecular Adsorbates Switch on Heterogeneous Catalysis: Induction of Reactivity by N-Heterocyclic Carbenes
Frank Glorius, Mizuki Tada, Gen-ichi Yokota, Christian Schwermann, Nikos L. Doltsinis, Satoshi Muratsugu, Johannes B. Ernst
We report the N-heterocyclic carbene (NHC)-induced activation of an otherwise unreactive Pd/Al2O3 catalyst. Surface analysis techniques demonstrate the NHC being coordinated to the palladium particles and affecting their electronic properties. Ab initio calculations provide further insight into the electronic effect of the coordination with the NHC injecting electron density into the metal nanocluster thus lowering the barrier for bromobenzene activation. By this NHC modification, the catalyst could be successfully applied in the Buchwald–Hartwig amination of aryl chlorides, bromides, and iodides. Various heterogeneity tests could additionally show that the reaction proceeds via a heterogeneous active species.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05112

DOI: 10.1021/jacs.7b05112

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