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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.621-628
Published online, 5th June, 2013
DOI: 10.3987/COM-13-S(S)10
Regioselectivity of the Intramolecular Biaryl Coupling Reaction of 3-Substituted Phenyl 2-Iodobenzoate using a Palladium Reagent

Kazuhiro Maeda, Takuya Matsukihira, Shumpei Saga, Yasuo Takeuchi,* Takashi Harayama, Yoshikazu Horino, and Hitoshi Abe*

*Department of Environmental Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan


This study investigated the regioselectivity of the intramolecular biaryl coupling reaction of the phenyl benzoate derivative which possesses a methyl or methoxy group at the meta-position of the phenoxy moiety. The type of base and the presence/absence of the phosphine ligand influenced the product ratio. A transition state model and the regioselectivity of the reaction are discussed.