Acetylenic Schmidt Reaction

By: William Sommer, Aldrich ChemFiles 2009, 9.5, 3.

Aldrich ChemFiles 2009, 9.5, 3.

Pyrroles are important synthons in the synthesis of natural products. Toste and co-workers utilized the affinity and electron-donating property to synthesize pyrroles via the acetylenic Schmidt reaction.1 Starting with an alkyl azide substrate and a bidentate digold complex as a catalyst, various substituted pyrroles were synthesized in good yields (Scheme 5). The conditions of the reaction are very mild using 2.5 mol % of catalyst in methylene chloride at 35 °C. It was noted that the reaction tolerates substitution of the alkyne with alkyl and aryl groups. Furthermore, substitution with electron-withdrawing and electrondonating groups did not have a notable affect on the yields of the final products.

Scheme 5.

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  1. Gorin, D. J. et al. J. Am. Chem. Soc. 2005, 127, 11260.

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