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.
