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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Multicomponent Photochemical Assembly of C(sp2)-S Substituted Imidazoles via Exciplex Formation
Illán Tagarro1, Helena F Piedra1, Daniel González-Pinardo2
1Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles" and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Oviedo, Oviedo 33006, Spain.
None:
We report a visible-light-driven multicomponent strategy for the synthesis of S-functionalized imidazoles from readily available organic halides, isothiocyanates, and isocyanides. The method operates under mild, photocatalyst-free conditions and exhibits broad substrate scope with excellent functional-group tolerance. Detailed mechanistic investigations support a reaction pathway involving direct photoexcitation of in situ generated thiophenolate intermediates and subsequent radical-based C-S bond formation. This process is likely governed by exciplex-type interactions rather than preassembled electron donor-acceptor complexes. Overall, this work introduces a distinct photochemical activation mode for C-S bond construction and expands the synthetic toolbox for accessing sulfur-containing heterocycles.
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