Formation of N-Heterocyclic Carbene–Boryl Radicals through Electrochemical and Photochemical Cleavage of the B–S bond in N-Heterocyclic Carbene–Boryl Sulfides
Journal of the American Chemical Society2013Vol. 135(45), pp. 16938–16947
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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
Abstract
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.
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