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Formation of N‑Heterocyclic Carbene–Boryl Radicals through Electrochemical and Photochemical Cleavage of the B–S bond in N‑Heterocyclic Carbene–Boryl Sulfides

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journal contribution
posted on 13.11.2013, 00:00 by Sofia Telitel, Anne-Laure Vallet, Stéphane Schweizer, Bernard Delpech, Nicolas Blanchard, Fabrice Morlet-Savary, Bernadette Graff, Dennis P. Curran, Marc Robert, Emmanuel Lacôte, Jacques Lalevée
The B–S bond in N-heterocyclic carbene (NHC)–boryl sulfides can be cleaved homolytically to NHC–boryl or NHC–thioboryl and thiyl radicals using light, either directly around 300 nm or with a sensitizer at a longer wavelength (>340 nm). In contrast, the electrochemical reductive cleavage of the B–S bond is difficult. This easy photolytic cleavage makes the NHC–boryl sulfides good type I photopolymerization initiators for the polymerization of acrylates under air.