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Mild Preparation of Haloarenes by Ipso-Substitution of Arylboronic Acids with N-Halosuccinimides

Christoph Thiebes, G. K. Surya Prakash*, Nicos A. Petasis, George A. Olah

*Loker Hydrocarbon Research Institute and Department of Chemistry, UniVersity of Southern California, Los Angeles, California 90089-1661, Email:

C. Thiebes, G. K. Surya Prakash, N. A. Petasis, G. A. Olah, Synlett, 1998, 141-142.

DOI: 10.1055/s-1998-1614


Aryl and heteroaryl boronic acids react with N-iodosuccinimide and N-bromosuccinimide to give the corresponding iodo- and bromo-arenes in good to excellent yields. The reaction is usually highly regioselective and yields only the ipso-substituted product.

see article for more examples

ipso-Nitration of Arylboronic Acids with Chlorotrimethylsilane-Nitrate Salts

G. K. S. Prakash, C. Panja, T. Mathew, V. Surampudi, N. A. Petasi, G. A. Olah, Org. Lett., 2004, 6, 2205-2207.

Key Words

Iodoarenes, N-Iodosuccinimide, Bromoarenes, N-Bromosuccinimide, Arylboronic acids, Ipso-substitution

ID: J60-Y1998-550