Practical approach for preparation of unsymmetric benzils from β-ketoaldehydes.

Libo Ruan, Min Shi, Nian Li, Xu Ding, Fan Yang, Jie Tang

Organic letters 2014 Feb 7

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An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones from β-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite.

Citation

Libo Ruan, Min Shi, Nian Li, Xu Ding, Fan Yang, Jie Tang. Practical approach for preparation of unsymmetric benzils from β-ketoaldehydes. Organic letters. 2014 Feb 7;16(3):733-5