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: gprakashusc.edu
C. Thiebes, G. K. Surya Prakash, N. A. Petasis, G. A. Olah, Synlett, 1998, 141-142.
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.
Iodoarenes, N-Iodosuccinimide, Bromoarenes, N-Bromosuccinimide, Arylboronic acids, Ipso-substitution