Highly E-Selective Alkene Isomerization Using Me4NF at Room Temperature

Leah Webster; Rofiat Ayoola Shoetan; Catherine M. Alder; Ruth L. Webster

doi:10.1021/acs.joc.5c02159

Highly E-Selective Alkene Isomerization Using Me₄NF at Room Temperature

Leah Webster, Rofiat Ayoola Shoetan, Catherine M. Alder, Ruth L. Webster

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Allylbenzene isomerization to trans-β-methylstyrene is catalyzed by Me₄NF (40 mol %) in dry CD₃CN under an inert atmosphere at room temperature, delivering high E-selectivity (E:Z = 100:0). The method tolerates diverse substituents but is limited by polar, protic groups. Some preliminary mechanistic studies are also reported.

Original language	English
Pages (from-to)	17198-17202
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	90
Issue number	48
Early online date	24 Nov 2025
DOIs	https://doi.org/10.1021/acs.joc.5c02159
Publication status	Published - 5 Dec 2025

Data Availability Statement

The data underlying this study are available in the published article, in its Supporting Information, and are openly available in the Open Science Framework repository, DOI: 10.17605/OSF.IO/3QTPY

Funding

GSK (RAS, CMA), the EPSRC (LW, RLW), and the Universities of Bath (RAS) and Cambridge (RLW) are thanked for funding.

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.5c02159Licence: CC BY

Cite this

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title = "Highly E-Selective Alkene Isomerization Using Me4NF at Room Temperature",

abstract = "Allylbenzene isomerization to trans-β-methylstyrene is catalyzed by Me4NF (40 mol \%) in dry CD3CN under an inert atmosphere at room temperature, delivering high E-selectivity (E:Z = 100:0). The method tolerates diverse substituents but is limited by polar, protic groups. Some preliminary mechanistic studies are also reported.",

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AB - Allylbenzene isomerization to trans-β-methylstyrene is catalyzed by Me4NF (40 mol %) in dry CD3CN under an inert atmosphere at room temperature, delivering high E-selectivity (E:Z = 100:0). The method tolerates diverse substituents but is limited by polar, protic groups. Some preliminary mechanistic studies are also reported.

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