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DOI: 10.1055/s-2003-42076
Rhenium-Catalyzed Epoxide Deoxygenation: Scope and Limitations
Publikationsverlauf
Publikationsdatum:
15. Oktober 2003 (online)
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Abstract
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 of functional groups including ketones (conjugated or non-conjugated to the new double bond), esters, nitriles, ethers, silyl ethers and phthalimides. Relative rates vary with substitution pattern and electronics; in general, monosubstituted and 2,2-disubstituted epoxides react fastest, and cis-2,3-disubstituted systems react faster than trans. Electron-withdrawing substituents promote the reaction.
Key words
epoxide deoxygenation - rhenium catalysis - O-atom transfer
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After 4 h, a trace of alkene was observed. However, the major product was reaction of the carbonyl oxygen to form 2-methyl-5-hydroxymethyloxazoline.