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

Aurodeep Panda; Caroline R Wood; William W Brennessel; William D Jones

doi:10.1021/acscatal.4c04572

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

ACS Catal. 2024 Oct 11;14(21):15927-15934. doi: 10.1021/acscatal.4c04572. eCollection 2024 Nov 1.

Authors

Aurodeep Panda¹, Caroline R Wood¹, William W Brennessel¹, William D Jones¹

Affiliation

¹ Department of Chemistry, University of Rochester, Rochester, New York 14627, United States.

Abstract

The air-stable copper(II) catalyst [Cu(^mesoFOX-L1)(MeCN)][OTf]₂ (2a) is prepared from a fused meso-dipyridylbisoxazolidine (^mesoFOX-L1) and CuBr₂, followed by treatment with AgOTf. The compound is a catalyst for the dehydration of 1-phenylethanol to styrene (+H₂O) 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.