P7. Reductive coupling of substituted acetophenones with TiCl_4 and Zn under Ultrasonication(Poster Presentation)

概要

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Using ultrasonication in oraganic reaction various ketones were reductively coupled to give the corresponding pinacol type dimer. Ketones were substituted with methyl, hydroxyl, acetoxy, halogen and amine on the benzene ring. Using ultrasonication, the reaction time changed shorter and the yields of the reductive coupling reaction changed better. The pinacol was converted to the corresponding pinacolone using strong acid, but pinacol did not change easily to pinacolone using ultrasonication with TiCl_4 in short time. In the case of acetophenone, the corresponding pinacol was obtained in 75% for 2h without using ultrasonication, however by using ultrasonication the same reductive coupling reaction of acetophenone was achieved in 90% only for 10 min. When acetophenone substituted with nitro group was used as the substitute, the nitropinacol produced in the reaction was easily reduced to aminopinachol in the reductive couppliung. Reductive coupling of fluoroacetophenone showed high yield in this reaction.
日本ソノケミストリー学会の論文
2011-10-15