Rhodium-Catalyzed β-Acylalkylation of Allylbenzene Derivatives with Allyl Alcohols via C-C Bond Cleavage

We report here a deallylative beta-acylalkylation reaction of allylbenzene derivatives with allyl alcohols in the presence of Cp*Rh catalysts. Allylbenzenes possessing pyridyl and pyrazolyl directing groups were converted to beta-aryl ketones via the cleavage of C(aryl)-C(allyl) bonds. Synthesis of a quinoline derivative from a beta-aryl ketone product bearing a pyrazolyl group was also achieved.

Automated summary

In this paper, a highly efficient deallylative beta-acylalkylation reaction of allylbenzene derivatives with allyl alcohols in the presence of Cp*Rh catalysts is reported. It was found that allylbenzene derivatives possessing pyridyl and pyrazolyl directing groups can be converted to beta-aryl ketones via cleavage of C(aryl)-C(allyl) bonds. Furthermore, synthesis of a quinoline derivative from a beta-aryl ketone product bearing a pyrazolyl group was also achieved.