Rhenium-Catalyzed Epoxide Deoxygenation: Scope and Limitations

• DOI: 10.1055/s-2003-42076
• Publication Date: 2003-10-29T07:52:53Z
• Authors: Kevin P. Gable; Eric C. Brown
• Keywords: Deoxygenation; Mesitylene

Transfer of oxygen atoms from epoxides to triphenyl­phosphine is efficiently catalyzed by Tp′ReO3 [Tp′ = hydrido-tris-(3,5-dimethylpyrazolyl)borate] in benzene at 75-105 ºC. The reaction tolerates a wide variety functional groups including ketones (conjugated or non-conjugated the new double bond), esters, nitriles, ethers, silyl ethers and phthalimides. Relative rates vary with substitution pattern electronics; general, monosub­stituted 2,2-disubstituted react fastest, cis-2,3-di­substituted systems faster than trans. Electron-withdrawing substituents promote reaction.