Advances in synthetic organic chemistry are tied to the discovery of novel reactivity. One such extensively explored reaction is 1,3-dipolar cycloaddition, reported in the early 20<sup>th</sup> century. Since 2001, interest in this field was reinvigorated following the discovery of the copper-catalyzed azide-alkyne cycloaddition. The ensuing finding of 1,2,3-triazoles bearing electron-withdrawing groups (such as a sulfonyl group) at the <i>N</i>1-position has been of particular interest due to the unusual chemical reactivity demonstrated by this family of heterocycles. Reactivity of such molecules under transition-metal free conditions has been recently explored. During our investigations, we observed an intriguing reaction of lithium acetylides and lithium triazolides to generate a spectrum of value-added organic molecules including cyclic sulfonamides and fused sultamoyl-indazoles. Further, we discovered facile aerobic oxidation of reactive intermediates leading to the elusive synthesis of α-hydroxy-amidines, α-keto-amidines, and novel imino-sultams. These new reactivity findings will be discussed in the presentation.

Building molecular complexity through simple chemical feedstocks: From cycloadditions to aerobic oxidations

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ACS Fall 2022

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