Solvent-dependent chemoselectivity in ruthenium-catalyzed cyclization of iodoalkyne-epoxide functionalities

Ming-Yuan Lin; Shambabu Joseph Maddirala; Rai-Shung Liu

doi:10.1021/ol050317+

Solvent-dependent chemoselectivity in ruthenium-catalyzed cyclization of iodoalkyne-epoxide functionalities

Org Lett. 2005 Apr 28;7(9):1745-8. doi: 10.1021/ol050317+.

Authors

Ming-Yuan Lin¹, Shambabu Joseph Maddirala, Rai-Shung Liu

Affiliation

¹ Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan 30043, Republic of China.

PMID: 15844896
DOI: 10.1021/ol050317+

Abstract

[reaction: see text] Treatment of 1-(2'-iodoethynylphenyl)-2-propyloxirane (3) with TpRuPPh(3)(CH(3)CN)(2)PF(6) 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-pi-iodoalkyne and ruthenium-2-iodovinylidene intermediates.