Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration
Aurodeep Panda, Ruilin Zhang, William W. Brennessel, William D. Jones
TL;DR
A new copper-based catalyst efficiently converts alcohols into olefins at low temperatures.
Contribution
A novel copper(II) quinoline-fused oxazolidine catalyst is developed for efficient alcohol dehydration.
Findings
The catalyst [Cu(QFOX)(CH3CN)][OTf]2 dehydrates alcohols at 120 °C with 1% loading.
It works on benzylic, allylic, tertiary, and unactivated secondary alcohols.
Copper(II) outperforms similar MnII, FeII, CoII, and NiII catalysts in dehydration activity.
Abstract
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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Taxonomy
TopicsCarbon dioxide utilization in catalysis · Asymmetric Hydrogenation and Catalysis · Oxidative Organic Chemistry Reactions