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

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Abstract

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.

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Key Words

Sulfonamides, Pyrroles

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ID: J54-Y2013-0390