Sonogashira Coupling of (Hetero)Aryl Bromosulfonyl Fluorides with Terminal Alkynes: Access to Dual-Functional SuFEx-Active Scaffolds

We report a general Sonogashira coupling strategy for the synthesis of structurally versatile alkynyl sulfonyl fluorides from (hetero)aryl bromosulfonyl fluorides and terminal alkynes. The reaction proceeds under mild conditions using Pd/Cu catalysis and exhibits broad functional group tolerance. The resulting scaffolds process two orthogonal reactive handles, an alkyne and a sulfonyl fluoride, that enable diverse post-functionalizations including hydrogenation, regioselective hydroiodination, oxidative cleavage to 1,2-diketones, and SuFEx-based conjugations. Notably, each reactive site can be selectively transformed without cross reactivity, highlighting their dual functional nature and synthetic utility of these SuFEx active building blocks.