Ringing the changes on DMAP

07 March 2005

4-(Dimethylamino)pyridine (DMAP) is a widely used reagent in organic synthesis, combining as it does, basicity with nucleophilicity. A recent article by Alan Spivey and Stellios Arseniyadis at Imperial College London* highlights the use of DMAP and related dialkylaminopyridines in catalysing the acylation (esterification) of alcohols.

It turns out that there is a complex interplay between catalyst structure, acylating agent, auxiliary base and solvent. So next time you use DMAP in such a reaction, be sure to test different reaction solvents, and if you get stuck, consider using alternative (albeit probably more expensive!) dialkylaminopyridines.

* A. Spivey and S. Arseniyadis, Angew. Chem. Int. Ed., 2004, 43, 5436-5441.