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Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage. 2007

Kenji Ueura, and Tetsuya Satoh, and Masahiro Miura
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

The oxidative coupling of benzoic acids with internal alkynes effectively proceeds in the presence of [Cp*RhCl2]2 and Cu(OAc)2 x H2O as catalyst and oxidant, respectively, to produce the corresponding isocoumarin derivatives. The copper salt can be reduced to a catalytic quantity under air. Interestingly, by using [Cp*IrCl2]2 in place of [Cp*RhCl2]2, the substrates undergo 1:2 coupling accompanied by decarboxylation to afford naphthalene derivatives exclusively. In this case, Ag2CO3 acts as an effective oxidant.

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