A method for catalytic conversion of C(aryl)−C(alkenyl) bonds in styrene derivatives to new C−C bonds is developed. In the presence of a rhodium catalyst, the alkenyl groups of styrenes bearing a pyrazolyl directing group were efficiently converted to other carbon substituents upon reacting with various alkenes including styrenes, aliphatic alkenes, and allyl alcohols. It is also indicated that the C−C bond cleavage proceeded via a hydrometalation/β-carbon elimination pathway.
We report here a deallylative β-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 β-aryl ketones via the cleavage of C(aryl)−C(allyl) bonds. Synthesis of a quinoline derivative from a β-aryl ketone product bearing a pyrazolyl group was also achieved.
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