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Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration
Aurodeep Panda1, Ruilin Zhang1, William W Brennessel1
1Department of Chemistry, University of Rochester, Rochester, New York 14627, United States.
None:
The new copper(II) catalyst [Cu(QFOX)(CH3CN)][OTf]2 has been synthesized and found to be active for alcohol dehydration to give olefins at 120 °C with a 1% catalyst loading (QFOX = di-2-quinolinyl-fused-oxazolidine). Benzylic, allylic, and tertiary alcohols are all dehydrated. In some cases, ethers are observed to be produced, but these are re-entrained into the catalytic cycle. Unactivated secondary alcohols are also dehydrated. Similar catalysts employing MnII, FeII, CoII, and NiII were also synthesized but showed reduced dehydration activity compared to the copper(II) derivative. A CuI analog was also prepared but did not show improved dehydration activity.
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