Chemodivergent Synthesis of β‑Phosphonyl Carboxylic Acids and Acylphosphine Oxides via Ring-Opening Addition of Cyclopropenone.

Siyu Zhang, Jiazhong Tang, Zhuo Huang, Shaotong Zhang, Qing-Wei Zhang

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Article in Precision chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

Siyu ZhangKey Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

Jiazhong TangKey Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

Zhuo HuangKey Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

Shaotong ZhangKey Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

Qing-Wei ZhangKey Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.ORCID https://orcid.org/0000-0002-8577-6304

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Chemodivergent synthesis offers a robust and efficient platform for streamlining synthetic routes and broadening reaction diversity. Herein, we demonstrate that the reaction of diphenylcyclopropanone with secondary phosphine oxides generates a versatile ketenylphosphorus intermediate, which serves as a pivotal platform for nucleophilic addition. This intermediate readily reacts with water and phosphine oxides, enabling efficient synthesis of structurally diverse β-phosphoryl carboxylic acids and acylphosphine oxides. Mechanistic studies and DFT calculations reveal a pivotal β-ketenyl phosphine oxide intermediate that undergoes selective nucleophilic addition, enabling divergent product formation.

Indexed as

chemodivergent synthesisβ-ketenyl phosphine oxideβ-phosphoryl acylphosphine oxidesβ-phosphoryl carboxylic acids

Identifiers

PMID41890405

DOI10.1021/prechem.5c00125

PMCPMC13014336

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