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2019•Organic LettersOpen access

Iron(II)/Persulfate Mediated Newman–Kwart Rearrangement

Thibault Gendron, Raul Pereira, Hafsa Yusuf Abdi, Timothy H. Witney, Erik Årstad

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Abstract

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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What this paper is about

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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Available abstract

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.

Key concepts: Chemistry, Persulfate, Stereochemistry, Organic chemistry, Catalysis

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