Chemodivergent Synthesis of β-Phosphonyl Carboxylic Acids and Acylphosphine Oxides via Ring-Opening Addition of Cyclopropenone
Year: 2025
Type: article
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.
Source: Precision Chemistry
Authors: Siyu Zhang, Jiazhong Tang, Zhuo Huang, Shaotong Zhang, Qing-Wei Zhang
Institution: University of Science and Technology of China
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4416530668