Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement

Thibault  Gendron; Raul Geraldo Pereira; Hafsa Abdi; Timothy Howard Witney; Erik Arstad

doi:10.1021/acs.orglett.9b04280

Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement

Thibault Gendron, Raul Geraldo Pereira, Hafsa Abdi, Timothy Howard Witney, Erik Arstad

Imaging Chemistry & Biology

UCL University College London

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

10 Citations (Scopus)

15 Downloads (Pure)

Abstract

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.

Original language	English
Pages (from-to)	274-278
Number of pages	5
Journal	ORGANIC LETTERS
Volume	22
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.9b04280
Publication status	Published - 3 Jan 2020

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10.1021/acs.orglett.9b04280

Iron(II)/Persulfate Mediated Newman-Kwart_GENDRON_Accepted12December2019_GOLD AAMAccepted author manuscript, 2.39 MBLicence: Unspecified

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abstract = "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.",

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AU - Arstad, Erik

PY - 2020/1/3

Y1 - 2020/1/3

N2 - 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.

AB - 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.

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Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement

Abstract

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