Efficient Dehydration of 1-Phenylethanol to Styrene by Copper(II) and Zinc(II) Fused-Bisoxazolidine Catalysts

The air-stable copper(II) catalyst [Cu(<sup>meso</sup>FOX-L1)(MeCN)][OTf]<sub>2</sub> (<b>2a</b>) is prepared from a fused meso-dipyridylbisoxazolidine (<sup>meso</sup>FOX-L1) and CuBr<sub>2</sub>, followed by treatment with AgOTf. The compound is a catalyst for the dehydration of 1-phenylethanol to styrene (+H<sub>2</sub>O) in over 95% yield at 1 mol % catalyst loading. Other alcohols (benzylic, tertiary, or allylic) are also efficiently dehydrated by this catalyst. Water separation in toluene solvent is found to play an important role in the reaction. Related compounds with Zn(II) have been prepared and display reduced dehydration activity.

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Publication Details

Journal
ACS Catalysis
Published
2024-10-11
DOI
https://doi.org/10.1021/acscatal.4c04572
Citations
4
Primary Topic
Catalysis for Biomass Conversion
Type
article
Field-Weighted Citation Impact
0.74

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article

Efficient Dehydration of 1-Phenylethanol to Styrene by Copper(II) and Zinc(II) Fused-Bisoxazolidine Catalysts

Ameesh Panda, William W. Brennessel, William D. Jones, Caroline R. Wood
4 citations
ACS Catalysis
Catalysis for Biomass Conversion
0.74
article

Efficient Dehydration of 1-Phenylethanol to Styrene by Copper(II) and Zinc(II) Fused-Bisoxazolidine Catalysts

Ameesh Panda, William W. Brennessel, William D. Jones, Caroline R. Wood
article en
4 citations

Abstract

The air-stable copper(II) catalyst [Cu(<sup>meso</sup>FOX-L1)(MeCN)][OTf]<sub>2</sub> (<b>2a</b>) is prepared from a fused meso-dipyridylbisoxazolidine (<sup>meso</sup>FOX-L1) and CuBr<sub>2</sub>, followed by treatment with AgOTf. The compound is a catalyst for the dehydration of 1-phenylethanol to styrene (+H<sub>2</sub>O) in over 95% yield at 1 mol % catalyst loading. Other alcohols (benzylic, tertiary, or allylic) are also efficiently dehydrated by this catalyst. Water separation in toluene solvent is found to play an important role in the reaction. Related compounds with Zn(II) have been prepared and display reduced dehydration activity.

ACS CatalysisVol. 14(21)
University of Rochester (US)
National Science Foundation, Chemical Sciences, Geosciences, and Biosciences Division
Clean water and sanitation
Openalex Percentile: Top 32%
Catalysis for Biomass Conversion
0.74
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