SDS of cas: 141556-42-5. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, is researched, Molecular C21H24N2, CAS is 141556-42-5, about Photoreduction of triplet thioxanthone derivative by azolium tetraphenylborate: a way to photogenerate N-heterocyclic carbenes. Author is Trinh, Thi Kim Hoang; Morlet-Savary, Fabrice; Pinaud, Julien; Lacroix-Desmazes, Patrick; Reibel, Corine; Joyeux, Cecile; Le Nouen, Didier; Metivier, Remi; Brosseau, Arnaud; Heroguez, Valerie; Chemtob, Abraham.
Although N-heterocyclic carbenes (NHCs) have brought profound changes in catalytic organic synthesis, their generation generally requires an inert atm. and harsh conditions. To overcome these limitations, an air-stable NHC photogenerator has been developed involving two mild components: 1,3-bis(mesityl)imidazolium tetraphenylborate (IMesH+BPh4-) and electronically excited isopropylthioxanthone (ITX). In this study, the photochem. mechanism is investigated via the accurate identification of the transient species and photoproducts. Electron transfer reaction between the excited triplet state of ITX and BPh4- is demonstrated as being the primary photochem. step. Nanosecond laser spectroscopy shows an efficient quenching and the formation of the expected ITX radical anion. The oxidized borane species is not observed, suggesting that this short-lived species could dissociate very rapidly to give the Ph radical – successfully identified using ESR – and triphenylborane. As regards the final photoproducts, 1H and 13C NMR spectroscopies support the formation of the targeted NHC, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes), suggesting the occurrence of a subsequent proton transfer reaction between ITX radical anion and imidazolium cation (IMesH+). Gas chromatog.-mass spectrometry reveals three other products: biphenyl, isopropylthioxanthene and ITX. Their formation can be reconciled with a 2-step mechanism of photoinduced electron/proton transfer reactions. 11B NMR spectroscopy demonstrates that the main organoboron photoproduct is diphenylborinic acid formed by oxidation of BPh3. Due to its Lewis acidity, Ph2BOH can react with IMes to yield an NHC-boron adduct.
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