Base Mediated Diazirination via Iodine(III) Reagents

Herein, we described an efficient method for the construction of highlyfunctionalized diazirines from the carbohydrazide and diazo-substituted hypervalentiodine reagents. Unambiguous transformation has been designed with user applicableand easy practicable conditions. Remarkably,D-glucose, menthol, aspirin, proline, andlithocholic acid were efficiently diazirinated. Furthermore, the method is mild, robust, and highly selective, which successfullyconverted a variety of aryl, alkyl, benzyl, and heterocyclic hydrazides into the corresponding diazirine derivatives.

Automated summary

Here, we described an efficient method for the construction of highly functionalized diazirines from carbohydrazide and diazo-substituted hypervalent iodine reagents. The method is user applicable and easy to practice with unambiguous transformation conditions. Notably, D-glucose, menthol, aspirin, proline, and lithocholic acid were efficiently diazirinated. Furthermore, the method is mild, robust, and highly selective, converting various aryl, alkyl, benzyl, and heterocyclic hydrazides into the corresponding diazirine derivatives.