Tuesday 15 July 2014

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

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.

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