Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 7, Pages 4720-4729Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00198
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Herein, an atom-economical intermolecular iron-catalyzed oxyamination of alkenes is reported. The insertion of oxygenated and nitrogenated moieties from the hydroxylamine substrate was observed with full regio- and chemo-selectivity for terminal alkenes in good yields. HFIP solvent appeared to synergistically promote the formation of the oxyaminated products with the iron catalyst. Preliminary mechanistic studies suggest a pathway involving aziridination followed by in situ ring opening.
An atom-economical intermolecular iron-catalyzed oxyamination of alkenes is described herein. The insertion of oxygenated and nitrogenated moieties from the hydroxylamine substrate was observed with full regio- and chemo-selectivity for terminal alkenes in good yields. HFIP as a solvent appeared to have a synergistic effect with the iron catalyst to promote the formation of the oxyaminated products. Preliminary mechanistic studies suggest a pathway going through an aziridination reaction followed by an in situ ring opening.
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