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A metal-free chemodifferentiating A
2BB' 4CR manifold forthe modular synthesis of tertiary skipped diynes is descri
bed.The manifold performs a triethylamine triggered reaction ofalkyl propiolates and acid chlorides to assem
ble two unitsof each component in the form of two propargylic alkynoates,a tertiary alcohol, and an ester. A differentiated incorporationof the two acid chloride components ensures functionaldiversity in the final structure. In addition, the presence oftwo connected propargylic alkynoates provides a reactiveplatform for complexity generation.