Visible-Light- and PPh₃-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature

Kartic Manna, Tanusree Ganguly, Sujoy Baitalik* and Ranjan Jana*

*Jadavpur University, Kolkata 700032; Indian Institute of Chemical Biology, Jadavpur, Kolkata 700032, West Bengal, India, Email: sujoy.baitalikjadavpuruniversity.in, rjanaiicb.res.in

K. Manna, T. Ganguly, S. Baitalik, R. Jana, Org. Lett., 2021, 23, 8634-8639.

DOI: 10.1021/acs.orglett.1c03343

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Abstract

Triphenylphosphine mediates a metal-free, intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature under visible-light irradiation without any photocatalyst. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.

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proposed mechanism

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Key Words

arylation, reduction of nitro compounds, triphenylphosphine

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ID: J54-Y2021