Practical approach for preparation of unsymmetric benzils from β-ketoaldehydes.
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.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University , Shanghai 200062, China.
Libo
L
Ruan
Min
M
Shi
Nian
N
Li
Xu
X
Ding
Fan
F
Yang
Jie
J
Tang
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D054879:Halogenation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010658:Phenylglyoxal / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012973:Sodium Hypochlorite / Q000737:chemistry*
D000447:Aldehydes; D007659:Ketones; D012973:Sodium Hypochlorite; D010658:Phenylglyoxal; C006697:benzil