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Synfacts 2025; 21(07): 708
DOI: 10.1055/a-2601-4456
Metals in Synthesis

Palladium-Catalyzed Formation of Phosphine Oxides Tethered to Tetrasubstituted Allenones

Contributor(s):
Mark Lautens 
,
Andrew G. Durant
Zhou S, Zou H, Huang X *, Qi J *, Xu Z. Liaocheng University, Shandong, P. R. China
Base-Promoted Regio- and Diastereoselective Synthesis of Tri- and Tetra-Substituted Homoallenyl Phosphine Oxides via Alkynyl Enones.

Org. Biomol. Chem. 2025;
23: 4718-4724
DOI: 10.1039/d5ob00446b
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Keywords

palladium - allenones - Heck reaction - two-step, one-pot

Significance

The synthesis of methylene-linked phosphine oxide tetrasubstituted allenones has been achieved. The reaction takes place in two steps. The first is the base-mediated hydrophosphinylation of alkynyl enones furnishing a trisubstituted allenone, which undergoes a Heck reaction to generate the final product.


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Comment

The authors were able to carry out the base-mediated reaction independent of the palladium reaction and isolate the trisubstituted allenone. Treatment of these intermediates with palladium and an aryl iodide in situ leads to the Heck reaction product, wherein the palladium(II) species migrates across to the less substituted double bond of the allene.


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Publication History

Article published online:
23 June 2025

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