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Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides
Santanu Ghosh1, Chandan K Jana1
1Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781039, India.
Abstract:
A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5'-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.
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