TY - JOUR
T1 - Rhenium-Catalyzed Epoxide Deoxygenation
T2 - Scope and Limitations
AU - Gable, Kevin P.
AU - Brown, Eric C.
PY - 2003
Y1 - 2003
N2 - 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 °C. 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.
AB - 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 °C. 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.
KW - Epoxide deoxygenation
KW - O-atom transfer
KW - Rhenium catalysis
UR - http://www.scopus.com/inward/record.url?scp=0242491547&partnerID=8YFLogxK
U2 - 10.1055/s-2003-42076
DO - 10.1055/s-2003-42076
M3 - Article
AN - SCOPUS:0242491547
SN - 0936-5214
SP - 2243
EP - 2245
JO - Synlett
JF - Synlett
IS - 14
ER -