tert-Butyl hydroperoxide mediated Wacker-type oxidations: taking advantage of hexafluoro-2-propanol for challenging substrates

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Org. Biomol. Chem., 2026, Advance ArticleDOI: 10.1039/D5OB01683E, Communication Open Access &nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Calum Maguire, Qun Cao, Selena C. L. Gilmer, Bill C. Hawkins, Peter C. Knipe, …

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tert-Butyl hydroperoxide mediated Wacker-type oxidations: taking advantage of hexafluoro-2-propanol for challenging substrates

* Corresponding authors

a School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast, UK
E-mail: [email protected], [email protected]

b College of Chemical Engineering, State Key Laboratory of Advanced Separation Membrane Materials, Zhejiang University of Technology, Hangzhou 310014, China

c Department of Chemistry, University of Otago, Dunedin 9054, New Zealand
E-mail: [email protected]

Abstract

Wacker-type oxidation of alkene substrates containing heteroatoms, such as allylic ethers, is challenging. Herein we describe the use of a dicationic Pd(II) complex, with tert-butyl hydroperoxide (TBHP) as the oxidant and how hexafluoro-2-propanol (HFIP) can improve performance. A series of substituted O-allylphenols and more complex derivatives were studied.