Abstract

Hydroboration of N-allyl-cis-2,6-dimethylpiperidine with HB(C6F5)2 gave the trimethylene-bridged frustrated N/B Lewis pair 7. It featured a trans-2,6-dimethyl substitution pattern at the piperidine unit which indicated preceding equilibration with its iminium cation/hydridoborate isomer 6 by means of an internal hydride transfer. In situ generated compound 6 is essential for the reaction with CO/HB(C6F5)2 to give the borataepoxide product 12 at the [N]–(CH2)3–[B] framework. The borataepoxide 12 reacts rapidly with CO2, cleaves the acidic C–H bond of a terminal alkyne, splits dihydrogen, and reacts with nitriles and benzaldehyde. Most products were characterized by X-ray diffraction.

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