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Issue 74, 2018
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Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner–Meerwein rearrangement

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Abstract

A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.

Graphical abstract: Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner–Meerwein rearrangement

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Publication details

The article was received on 12 Jul 2018, accepted on 20 Aug 2018 and first published on 21 Aug 2018


Article type: Communication
DOI: 10.1039/C8CC05634J
Citation: Chem. Commun., 2018,54, 10503-10506
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    Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner–Meerwein rearrangement

    X. Fan, Q. Wang, Y. Wei and M. Shi, Chem. Commun., 2018, 54, 10503
    DOI: 10.1039/C8CC05634J

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