In situ generation of the Ohira-Bestmann reagent from stable sulfonyl azide: scalable synthesis of alkynes from aldehydes.

We report an improved method for in situ generation of the Ohira-Bestmann reagent. Using the recently reported bench-stable imidazole-1-sulfonyl azide as diazotransfer reagent, this new method represents a scalable and convenient approach for the transformation of aldehydes into terminal alkynes. The method features an easier workup compared to the existing in situ protocol due to increased aqueous solubility of waste products.