Alumina-Mediated π-Activation of Alkynes

Akhmetov V, Feofanov M, Sharapa D, Amsharov K (2021)

Publication Type: Journal article

Publication year: 2021

Journal

Journal of the American Chemical Society American Chemical Society

DOI: 10.1021/jacs.1c07845

Abstract

The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3 activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.

Authors with CRIS profile

Vladimir Akhmetov Lehrstuhl für Organische Chemie II Mikhail Feofanov Lehrstuhl für Organische Chemie II Konstantin Amsharov

Involved external institutions

Karlsruhe Institute of Technology (KIT) DE Germany (DE) Martin-Luther-Universität Halle-Wittenberg (MLU) DE Germany (DE)

How to cite

APA:

Akhmetov, V., Feofanov, M., Sharapa, D., & Amsharov, K. (2021). Alumina-Mediated π-Activation of Alkynes. Journal of the American Chemical Society. https://dx.doi.org/10.1021/jacs.1c07845

MLA:

Akhmetov, Vladimir, et al. "Alumina-Mediated π-Activation of Alkynes." Journal of the American Chemical Society (2021).

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