A one-pot conversion of alkyl azides to diazo compounds is outlined. After azido group protection of α-azidocarbonyl compounds, treatment of the resulting phosphazides with silica gel in a wet solvent afforded α-diazo carbonyl products by azide-deprotective conversion. Competitive reactions of α-azido amides with alkyl and aryl azides demonstrate azide-site selectivity. Azide-site selective click functionalization by this one-pot sequence is also demonstrated with diazido compounds.
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Tanimoto et al. (2024) studied this question.
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