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Solvent-Dependent Chemoselectivity in Ruthenium-Catalyzed Cyclization of Iodoalkyne−Epoxide Functionalities

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journal contribution
posted on 28.04.2005, 00:00 by Ming-Yuan Lin, Shambabu Joseph Maddirala, Rai-Shung Liu
Treatment of 1-(2-iodoethynylphenyl)-2-propyloxirane (3) with TpRuPPh3(CH3CN)2PF6 catalyst (10 mol %) produced 1-iodo-2-naphthol (3a) exclusively in DMF, but gave 2-iodobenzo[d]oxepin (3b) efficiently in benzene. Such a solvent-dependent chemoselectivity suggests a solution equilibrium between ruthenium−π-iodoalkyne and ruthenium−2-iodovinylidene intermediates.