Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration

Panda, Aurodeep; Zhang, Ruilin; Brennessel, William W.; Jones, William D.

doi:10.1021/acs.joc.5c02669

Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration

Journal Article · Wed Dec 31 00:00:00 EST 2025 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/acs.joc.5c02669· OSTI ID:3014209

Panda, Aurodeep ^[1]; Zhang, Ruilin ^[1]; ^[1]; ^[1]

University of Rochester, NY (United States)

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 Mn^II, Fe^II, Co^II, and Ni^II were also synthesized but showed reduced dehydration activity compared to the copper(II) derivative. A Cu^I analog was also prepared but did not show improved dehydration activity.

View Accepted Manuscript (DOE)

Research Organization:: University of Rochester, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: SC0020230

OSTI ID:: 3014209

Journal Information:: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 2 Vol. 91; ISSN 0022-3263; ISSN 1520-6904

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration

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