Reagent-Controlled Reversal of Regioselectivity in Nucleophilic Fluorination of Spiro-epoxyoxindole: Synthesis of 3‑Fluoro-3-hydroxymethyloxindole and 3‑Aryl-3-fluoromethyloxindole

Reagent-Controlled Reversal of Regioselectivity in Nucleophilic Fluorination of Spiro-epoxyoxindole: Synthesis of 3‑Fluoro-3-hydroxymethyloxindole and 3‑Aryl-3-fluoromethyloxindole

A convenient and metal/catalyst-free approach for the reversal of regioselectivity in nucleophilic fluorination of a wide range of spiro-epoxyoxindoles has been reported simply by altering the nucleophilic fluoride reagents. Py·(HF) x -mediated fluorination at the tertiary sp3-C center of spiro-epox...

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Veröffentlicht in:Journal of organic chemistry 2019-02, Vol.84 (4), p.2252-2260
Hauptverfasser: Hajra, Saumen, Roy, Sayan, Maity, Subrata, Chatterjee, Sandip
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container_title Journal of organic chemistry
container_volume 84
creator Hajra, Saumen
Roy, Sayan
Maity, Subrata
Chatterjee, Sandip
description A convenient and metal/catalyst-free approach for the reversal of regioselectivity in nucleophilic fluorination of a wide range of spiro-epoxyoxindoles has been reported simply by altering the nucleophilic fluoride reagents. Py·(HF) x -mediated fluorination at the tertiary sp3-C center of spiro-epoxyoxindole furnishes 3-fluoro-3-hydroxymethyloxindoles, whereas TBAF-mediated fluoride addition at the primary sp3-C center renders 3-fluoromethyl-3-hydroxyoxindoles, which have been utilized for the synthesis of 3-aryl-3-fluoromethyloxindole.
doi_str_mv 10.1021/acs.joc.9b00059
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title Reagent-Controlled Reversal of Regioselectivity in Nucleophilic Fluorination of Spiro-epoxyoxindole: Synthesis of 3‑Fluoro-3-hydroxymethyloxindole and 3‑Aryl-3-fluoromethyloxindole
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