Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes

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 http://pubs.acs.org/doi/abs/10.1021/ol403762e

Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes

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

pp 733–735

Publication Date (Web): January 29, 2014 (Letter)

DOI: 10.1021/ol403762e

 

 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.