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

Chemical Communications : Chem Comm
Xing FanMin Shi

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.

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Citations

Dec 29, 2020·Chemical Communications : Chem Comm·Neshat Rozatian, David R W Hodgson
Jul 15, 2021·Organic & Biomolecular Chemistry·Swarnayu BanikB V Subba Reddy
Aug 14, 2021·Beilstein Journal of Organic Chemistry·Teruo UmemotoGerald B Hammond
Jul 3, 2020·Organic Letters·Qi ZhangYajun Li

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Methods Mentioned

BETA
NMR
X-ray

Software Mentioned

Selectfluor

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