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March 23, 2026The Journal of Organic Chemistry2 citations

Palladium Catalyzed Asymmetric C(sp)–P Cross-Coupling via Kinetic Resolution of Secondary Phosphine Oxides

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JGJianguo GuYWYuen WuZTZhou Tang

Key Points

  • The central aim is to develop a palladium-catalyzed reaction for synthesizing P-stereogenic alkynyl phosphine oxides.
  • Utilized palladium as a catalyst for cross-coupling reactions.
  • Employed secondary phosphine oxides and alkynyl chlorides as key reactants.
  • Conducted the reaction under mild conditions to enhance product formation.
  • Achieved products with enantioselectivity up to 94% ee.
  • Demonstrated good functional group tolerance in the reaction.
  • Generated valuable chiral alkynyl phosphorus compounds efficiently.

Abstract

Herein, we report a palladium-catalyzed asymmetric C(sp)-P cross-coupling reaction between secondary phosphine oxides (SPOs) and alkynyl chlorides, providing a direct and efficient route to access P-stereogenic alkynyl phosphine oxides via a kinetic resolution process. This method proceeds under mild conditions, delivering products with excellent enantioselectivity (up to 94% ee) and good functional group tolerance. This work offers a straightforward and modular strategy for the synthesis of valuable chiral alkynyl phosphorus compounds.

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Cite This Study

Gu et al. (2026) studied this question.

synapsesocial.com/papers/69c0de74fddb9876e79c138fhttps://doi.org/10.1021/acs.joc.6c00057
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