18036-85-6Relevant articles and documents
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.