Rhodium- and Iridium-Catalyzed Oxidative Coupling of Benzoic Acids with Alkynes via Regioselective C−H Bond Cleavage
The Journal of Organic Chemistry2007Vol. 72(14), pp. 5362–5367
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Abstract
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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