Iodide as an Activating Agent for Acid Chlorides in Acylation Reactions
Russell J. Wakeham, James E. Taylor, Steven D. Bull*, James A. Morris and Jonathan M. J. Williams*
*Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom, Email: j.m.j.williamsbath.ac.uk
R. J. Wakeham, J. E. Taylor, S. D. Bull, J. A. Morris, J. M. J. Williams, Org. Lett., 2013, 15, 702-705.
DOI: 10.1021/ol400035f (free Supporting Information)
see article for more reactions
Acid chlorides can be activated to transient acid iodide intermediates using a simple iodide source. This indermediates undergo nucleophilic attack from a variety of relatively weak nucleophiles - including Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives.
see article for more examples