1435392-63-4Relevant academic research and scientific papers
Aryl imidazylates and aryl sulfates as electrophiles in metal-free ArSN1 reactions
Qrareya, Hisham,Protti, Stefano,Fagnoni, Maurizio
, p. 11527 - 11533 (2014)
Some oxygen-bonded substituents were investigated as leaving groups in photoinduced ArSN1 reactions. Irradiation of aryl imidazylates and of the corresponding imidazolium salts mainly caused homolysis of the ArO-S bond. However, previously unexplored trifluoroethoxy aryl sulfates were found to undergo efficient metal-free arylation. The sulfates were conveniently generated in situ by dissolving the corresponding imidazolium salts in basic 2,2,2-trifluoroethanol.
Metal-free arylations via photochemical activation of the Ar-OSO 2R bond in aryl nonaflates
Raviola, Carlotta,Canevari, Veronica,Protti, Stefano,Albini, Angelo,Fagnoni, Maurizio
, p. 2704 - 2708 (2013/10/08)
The photolysis of electron-rich aryl nonaflates (ArONfs) in protic media was investigated and heterolysis of the Ar-OS bond (from 3ArONf) took place. The reaction generated a triplet phenyl cation that added to π-bond nucleophiles. This metal-free arylation method was made further useful by adopting in situ preparation of ArONf from the corresponding phenol.
Transition-metal-free arylations via photogenerated triplet 4-alkyl- and 4-trimethylsilylphenyl cations
Qrareya, Hisham,Raviola, Carlotta,Protti, Stefano,Fagnoni, Maurizio,Albini, Angelo
, p. 6016 - 6024 (2013/07/26)
The irradiation in protic solvents of 4-chloroalkylbenzenes and 4-chlorophenyltrimethylsilane caused the heterolytic cleavage of aryl-chlorine bonds to give the corresponding triplet phenyl cations. These were exploited for transition-metal-free arylation reactions under mild conditions to give allylbenzenes, γ-benzyl lactones, 3-arylacetals (ketals), and biaryls in moderate to good yields. The path followed was supported by DFT calculations at the UB3LYP/6-311+G(2d,p) level.
