Synthesis of phenanthrone derivatives from sec-alkyl aryl ketones and aryl halides via a palladium-catalyzed dual C-H bond activation and enolate cyclization
Gandeepan, P.; Parthasarathy, K.; Cheng, C.-H.
Journal of the American Chemical Society 132(25): 8569-8571
A palladium-catalyzed chelation-assisted C-H activation of alkyl aryl ketones and their reaction with aryl iodides to afford ortho-arylated products is described. For sec-alkyl aryl ketones, the catalytic reaction proceeds further to give 10,10-dialkylphenanthrone derivatives. A possible reaction mechanism involving directed dual C-H bond activation and enolate cyclization for the formation of 10,10-dialkylphenanthrone derivatives is proposed.