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Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

preprint
submitted on 22.09.2020 and posted on 23.09.2020 by Alexandra Millimaci, Rowan Meador, Sara Dampf, John D. Chisholm

4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt’s salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochemistry of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials.

History

Email Address of Submitting Author

jdchisho@syr.edu

Institution

Syracuse University

Country

USA

ORCID For Submitting Author

0000-0001-9518-2393

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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