Unveiling the Use of 1,1-Bis(triflyl)ethylene as CF3SO2CH═CH2 Source with the Assistance of (n-Bu)4NF: Synthesis of 3-[(Trifluoromethyl)sulfonyl]cyclobut-1-enes.

Allylic sulfone-embedded cyclobutenes have been prepared in one pot from alkynes. The carbocycle and the alkenyl sulfone moieties were installed through consecutive bis(triflyl)cyclobutenylation of a triple bond and tetra-n-butylammonium fluoride (TBAF)-assisted hydrodesulfonylation of an allylic bis(sulfone). It is noteworthy that 1,1-bis(triflyl)ethylene acts as a CF3SO2CH═CH2 source for the first time.

Straightforward Synthesis of Bis[(trifluoromethyl)sulfonyl]ethylated Isocoumarins from 2-Ethynylbenzoates.

Herein, we report a facile isocoumarin and isoquinolone preparation by taking advantage of an initial bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] reaction, followed by heterocyclization, which contrasts with our previous results on cyclobutene formation. The efficiency of the catalyst- and irradiation-free heterocyclization/bis(triflyl)ethylation sequence showed exquisite dependence on the electronic nature of the substituents at the 2-ethynylbenzoate(benzamide) precursors. Molecular docking of model bis(triflyl)ethylated isocoumarins on human acetylcholinesterase (hAChE) revealed promising biological activities through selective coordination on both the catalytic active site and peripheral active site.