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. 2025 Sep 9;15(39):32424-32430.
doi: 10.1039/d5ra05242d. eCollection 2025 Sep 5.

Base mediated approach for the synthesis of deoxybenzoins using γ-aryl-β-ketoesters and benzoyl chlorides

Shailendra Singh Choudhary  1   2 , Ratanamala S Darole  1   2 , Gamidi Rama Krishna  1 , Beeran Senthilkumar  1   2
Affiliations

Base mediated approach for the synthesis of deoxybenzoins using γ-aryl-β-ketoesters and benzoyl chlorides

Shailendra Singh Choudhary et al. RSC Adv. .

Abstract

This study introduces a one-pot, transition metal-free strategy for synthesizing deoxybenzoins, overcoming the challenges of conventional methods. The reaction involves dual acylation of γ-aryl β-keto esters using K2CO3 in dioxane at 90 °C, followed by a concerted transformation to form deoxybenzoin. The protocol operates under mild conditions, tolerates a broad range of substrates, and produces minimal by-products, making it a practical, scalable alternative for accessing pharmaceutically relevant deoxybenzoins.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Fig. 1
Fig. 1. Biologically active moieties containing deoxybenzoin building block.
Fig. 2
Fig. 2. Synthetic utility of deoxybenzoins.
Scheme 1
Scheme 1. Previous reports and present work.
Fig. 3
Fig. 3. 2-Chloropyridines, which were unproductive under the optimized reaction conditions.
Scheme 2
Scheme 2. Gram-scale synthesis of compound 3a.
Scheme 3
Scheme 3. Control experiment.
Scheme 4
Scheme 4. Proposed reaction mechanism.
See this image and copyright information in PMC

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