Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement.

[en] 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 offers immediate practical benefits to access functionalized thiophenols.

Disciplines :

Chemistry
Radiology, nuclear medicine & imaging

Author, co-author :

Gendron, Thibault ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique-nucléaire ; Centre for Radiopharmaceutical Chemistry , University College London , 5 Gower Place , London WC1E 6BS , United Kingdom ; Department of Chemistry , University College London , 20 Gordon Street , London WC1H 0AJ , United Kingdom

Pereira, Raul ; Centre for Advanced Biomedical Imaging , University College London , 72 Huntley Street , London WC1E 6DD , United Kingdom ; Department of Imaging Chemistry and Biology, School of Biomedical Engineering & Imaging Sciences , King's College London , St. Thomas' Hospital , London SE1 7EH , United Kingdom

Abdi, Hafsa Y ; Department of Chemistry , University College London , 20 Gordon Street , London WC1H 0AJ , United Kingdom

Witney, Timothy H ; Centre for Advanced Biomedical Imaging , University College London , 72 Huntley Street , London WC1E 6DD , United Kingdom ; Department of Imaging Chemistry and Biology, School of Biomedical Engineering & Imaging Sciences , King's College London , St. Thomas' Hospital , London SE1 7EH , United Kingdom

Årstad, Erik ; Centre for Radiopharmaceutical Chemistry , University College London , 5 Gower Place , London WC1E 6BS , United Kingdom ; Department of Chemistry , University College London , 20 Gordon Street , London WC1H 0AJ , United Kingdom

Language :

English

Title :

Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement.

Publication date :

03 January 2020

Journal title :

Organic Letters

ISSN :

1523-7060

eISSN :

1523-7052

Publisher :

American Chemical Society, United States

Volume :

Issue :

Pages :

274 - 278

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://pubs.acs.org/doi/pdf/10.1021/acs.orglett.9b04280

European Projects :

FP7 - 602102 - EPITARGET - Targets and biomarkers for antiepileptogenesis

Funders :

EPSRC - Engineering and Physical Sciences Research Council
BCRF - Breast Cancer Research Foundation
EU - European Union
Wellcome Trust

Funding number :

602102; 107610/Z/15/Z; C1519/A16463; C2536/A10337

Funding text :

We thank Dr Laure Benhamou (Department of Chemistry, University College London) and Dr. Julie Charpentier (Givaudan) for helpful discussions. We thank the mass spectrometry facility at King’s College London for assistance with the HRMS, ICP-MS and MS/MS experiments. The research leading to these results was funded by the European Union’s Seventh Framework Programme (FP7/2007-2013) under Grant Agreement No. 602102 (EPITARGET) (E.A.), a Wellcome Trust and Royal Society Sir Henry Dale Fellowship (107610/Z/15/Z) to (T.H.W.), CRUK & EPSRC Comprehensive Cancer Imaging Centre at KCL, UCL & Imperial jointly funded by Cancer Research UK and the Engineering and Physical Sciences Research Council (EPSRC; C1519/A16463; C2536/A10337) (T.G.), and the UCL MSci in Chemistry (H.Y.A.). This work was undertaken at UCLH/UCL, which is funded in part by the Department of Health’s NIHR Biomedical Research Centres funding scheme.
Royal Society Sir Henry Dale Fellowship

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since 01 December 2022

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