Transition-Metal-Free Arylations via Photogenerated Triplet 4‑Alkyl- and 4‑Trimethylsilylphenyl Cations
journal contributionposted on 2013-06-21, 00:00 authored by Hisham Qrareya, Carlotta Raviola, Stefano Protti, Maurizio Fagnoni, Angelo Albini
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.