Issue 74, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
12 Jul 2018
Accepted
20 Aug 2018
First published
21 Aug 2018

Chem. Commun., 2018,54, 10503-10506

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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