Issue 26, 2015

Radical aminooxygenation of alkenes with N-fluoro-benzenesulfonimide (NFSI) and TEMPONa

Abstract

Reaction of various alkenes with commercially available N-fluorobenzenesulfonimide (NFSI) and TEMPONa provides the corresponding aminooxygenation products in moderate to good yields. Single electron transfer from readily generated TEMPONa to NFSI allows for clean generation of the corresponding bissulfonylamidyl radical along with TEMPO. N-radical addition to an alkene and subsequent TEMPO trapping provides the corresponding aminooxygenation product.

Graphical abstract: Radical aminooxygenation of alkenes with N-fluoro-benzenesulfonimide (NFSI) and TEMPONa

Supplementary files

Article information

Article type
Communication
Submitted
21 Jan 2015
Accepted
16 Feb 2015
First published
17 Feb 2015

Chem. Commun., 2015,51, 5706-5709

Author version available

Radical aminooxygenation of alkenes with N-fluoro-benzenesulfonimide (NFSI) and TEMPONa

Y. Li, M. Hartmann, C. G. Daniliuc and A. Studer, Chem. Commun., 2015, 51, 5706 DOI: 10.1039/C5CC00591D

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