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

Jimin Han, Jongwon Kim, Jaehoo Lee, Younghun Kim, Sarah Yunmi Lee

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9 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)15476-15487
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number23
DOIs
Publication statusPublished - 2020 Dec 4

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society. All rights reserved.

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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