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The oxidative coupling of benzoic acids with alkynes and alkenes effectively proceeds in the presence of a Rh catalyst and an appropriate oxidant to produce the corresponding isocoumarin and phthalide derivatives, respectively. Interestingly, by using an Ir catalyst in place of Rh, the acids and alkynes undergo 1:2 coupling accompanied by decarboxylation to afford naphthalene derivatives exclusively.
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Satoh et al. (2008) studied this question.
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