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A Practical Iron-Based Newman-Kwart Rearrangement Under Oxidative Conditions

preprint
submitted on 23.10.2019 and posted on 29.10.2019 by Thibault Gendron, Raul Pereira, Hafsa Yusuf Abdi, Timothy Witney, Erik Arstad
Herein, we report that iron(II)/ammonium persulfate in aqueous acetonitrile mediates the Newman-Kwart rearrangement of O-aryl carbamothioates. Electron-rich substrates react rapidly under moderate heating to afford the rearranged products in excellent yields. The mild conditions, rapid reaction rates, and suitability for scale up offer immediate practical benefits to access functionalised thiophenols.

Funding

Detecting tumour resistance to treatment with positron emission tomography.

Wellcome Trust

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CRUK & EPSRC C1519/A16463

CRUK & EPSRC C2536/A10337

NIHR University College London Hospitals Biomedical Research Centre

NIHR Central Commissioning Facility

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History

Email Address of Submitting Author

tim.witney@kcl.ac.uk

Institution

King's College London

Country

United Kingdom

ORCID For Submitting Author

0000-0002-9475-2873

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Initial submission

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in Organic Letters

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