Guanidinium iodide/urea hydrogen peroxide-catalyzed azidation of β-dicarbonyl compounds with trimethylsilyl azide

We present an efficient synthesis of α-azido-β-dicarbonyl compounds from β-dicarbonyl compounds and trimethylsilyl azide, catalyzed by guanidinium hypoiodite. The reaction can be run in air at ambient temperature (up to 40 °C) and is not sensitive to moisture. The substrate scope is broad, including cyclic and linear β-dicarbonyl compounds, and the α-azide products are obtained in 55%-99% yield.

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