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N-Halosuccinimide/BF3-H2O, Efficient Electrophilic Halogenating Systems for Aromatics

G. K. Surya Prakash,* Thomas Mathew, Dushyanthi Hoole, Pierre M. Esteves, Qi Wang, Golam Rasul and George A. Olah

*Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, Email: gprakashusc.edu

G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esteves, Q. Wang, G. Rasul, G. A. Olah, J. Am. Chem. Soc., 2004, 126, 15770-15776.

DOI: 10.1021/ja0465247 (free Supporting Information)


Abstract

N-Halosuccinimides are efficiently activated in trifluoromethanesulfonic acid and BF3-H2O, allowing the halogenations of deactivated aromatics. BF3-H2O is more economic, easy to prepare, nonoxidizing, and offers sufficiently high acidity.

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Key Words

Chlorination, Bromination, Iodination, NBS, NCS, NIS


ID: J48-Y2004-1870