Efficient Dehydration\nof 1‑Phenylethanol to\nStyrene 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\na fused meso-dipyridylbisoxazolidine\n(<sup>meso</sup>FOX-L1) and CuBr<sub>2</sub>, followed by treatment\nwith AgOTf. The compound is a catalyst for the dehydration of 1-phenylethanol\nto styrene (+H<sub>2</sub>O) in over 95% yield at 1 mol % catalyst\nloading. Other alcohols (benzylic, tertiary, or allylic) are also\nefficiently dehydrated by this catalyst. Water separation in toluene\nsolvent is found to play an important role in the reaction. Related\ncompounds with Zn(II) have been prepared and display reduced dehydration\nactivity.

Publication Details

Journal
Figshare
Published
2024-10-11
DOI
https://doi.org/10.1021/acscatal.4c04572.s001
Primary Topic
Chemical Synthesis and Reactions
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article
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article

Efficient Dehydration\nof 1‑Phenylethanol to\nStyrene by Copper(II) and Zinc(II) Fused-Bisoxazolidine Catalysts

Figshare
Chemical Synthesis and Reactions
article

Efficient Dehydration\nof 1‑Phenylethanol to\nStyrene by Copper(II) and Zinc(II) Fused-Bisoxazolidine Catalysts

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Abstract

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

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Efficient Dehydration\nof 1‑Phenylethanol to\nStyrene by Copper(II) and Zinc(II) Fused-Bisoxazolidine Catalysts · Figshare (2024) | TGRS Research Map | TGRS