A chromatographic relay conjugated photoredox strategy: S, Se-pharmacophore from alkenes via formal [2+ 2+ 1] heteroannulation

IU Hoque, S Debnath, R Lo, S Maity - Chemical Communications, 2024 - pubs.rsc.org
IU Hoque, S Debnath, R Lo, S Maity
Chemical Communications, 2024pubs.rsc.org
An expedient route to 2-aminodihydrothiophenes and their seleno analogues is reported. A
three-component photoredox reaction between alkene, thio (seleno) cyanate, and
bromomalonate is employed, generating a carbo-thio (seleno) cyanate intermediate that
undergoes a domino of reactions mediated by alumina column chromatography, leading to
valuable chalcogen pharmacophores. Mechanistic investigations using DFT and control
experiments reveals an intramolecular H-bond responsible for driving the domino forward.
An expedient route to 2-aminodihydrothiophenes and their seleno analogues is reported. A three-component photoredox reaction between alkene, thio(seleno)cyanate, and bromomalonate is employed, generating a carbo-thio(seleno)cyanate intermediate that undergoes a domino of reactions mediated by alumina column chromatography, leading to valuable chalcogen pharmacophores. Mechanistic investigations using DFT and control experiments reveals an intramolecular H-bond responsible for driving the domino forward.
The Royal Society of Chemistry
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