Solvent-Dependent Chemoselectivity in Ruthenium-Catalyzed Cyclization of Iodoalkyne−Epoxide Functionalities
journal contributionposted on 28.04.2005 by Ming-Yuan Lin, Shambabu Joseph Maddirala, Rai-Shung Liu
Any type of content formally published in an academic journal, usually following a peer-review process.
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.