Visible-Light- and PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature
Kartic Manna1,2, Tanusree Ganguly3, Sujoy Baitalik3
1Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India.
Abstract:
We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.
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