In the last decades, the alkynylation of nitrogen-based nucleophiles has been the focus of intensive research due to the synthetic versatility of the formed ynamines/ynamides products. Most methods relied on copper-catalysis with free or pre-activated alkynes (including halides, carboxylic acid, organometallic reagents and hypervalent iodine reagents (HIR), Scheme 1A). 1 Among the potential coupling partners capable of transferring alkynes, HIR particularly attracted attention as they allowed the use of milder reaction conditions. While alkynylation using mononitrogen-based nucleophiles is well established, only few examples of the synthesis of ynehydrazides are reported. Initial attempts to alkynylate hydrazides with alkynyl HIR or bromalkynes required harsh conditions and/or afforded the products in poor yields. To circumvent this issue, Batey and Beveridge followed an Umpolung strategy using azodicarboxylates as hydrazide precursors and acetylides nucleophiles (Scheme 1B). The obtained products could then be used in diverse applications. 3e-h However, this transformation was limited to symmetrical azodicarboxylates and required a strong base. Therefore, the development of a milder protocol suitable for non-symmetrical hydrazides would be beneficial.