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Boron Lewis Acid-Catalyzed Hydrophosphinylation of N‑Heteroaryl-Substituted Alkenes with Secondary Phosphine Oxides

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journal contribution
posted on 12.11.2020, 15:22 by Jimin Han, Jongwon Kim, Jaehoo Lee, Younghun Kim, Sarah Yunmi Lee
We report the boron-catalyzed hydrophosphinylation of N-heteroaryl-substituted alkenes with secondary phosphine oxides that furnishes various phosphorus-containing N-heterocycles. This process proceeds under mild conditions and enables the introduction of a phosphorus atom into multisubstituted alkenylazaarenes. The available mechanistic data can be explained by a reaction pathway wherein the C–P bond is created by the reaction between the activated alkene (by coordination to a boron catalyst) and the phosphorus­(III) nucleophile (in tautomeric equilibrium with phosphine oxide).