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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

2010

ISSN/ISBN: 1520-5126
PMID: 20524609
DOI: 10.1021/ja1026248
Accession: 056080974
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.

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