Reductive Deamination with Hydrosilanes Catalyzed by B(C₆F₅)₃

Huaquan Fang, Martin Oestreich

*Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany, Email: martin.oestreichtu-berlin.de

H. Fang, M. Oestreich, Angew. Chem. Int. Ed., 2020, 59, 11394-11398.

DOI: 10.1002/anie.202004651

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Abstract

B(C₆F₅)₃ catalyzes dehydrogenative couplings of certain amines and hydrosilanes at elevated temperatures. At higher temperature, the dehydrogenation pathway competes with cleavage of the C-N bond and defunctionalization is obtained. This can be turned into a useful methodology for the transition-metal-free reductive deamination of a broad range of amines.

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General Procedure for the Reductive Deamination

In a nitrogen-filled glovebox, a 1.00-mL dried sealed tube was charged with the desired amount of amine, hydrosilane, 1,2-C₆H₄F₂, and B(C₆F₅)₃. The sealed tube was sealed tightly with a teflon plug, and the mixture was stirred at 120 °C for 24 h. After the resulting reaction mixture was cooled to room temperature, mesitylene (0.500 equiv) was added as an internal standard, and the yield was determined by NMR spectroscopy from the ¹H NMR spectrum. The residue was purified by flash column chromatography on silica gel with n-pentane as the eluent to give the corresponding hydrocarbon.

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Key Words

deamination, phenylsilane

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ID: J06-Y2020