Authors
Hisham Qrareya
Carlotta Raviola
Stefano Protti
Maurizio Fagnoni
and Angelo Albini.
Pages From
6016
Pages To
6024
Journal Name
The Journal of Organic Chemistry (JOC).
Volume
78
Issue
12
Keywords
triplet phenyl cations, γ-benzyl lactones, transitionmetal-free arylation, DFT
Project
This work has been supported by the Fondazione Cariplo (Grant No. 20111839).
Abstract

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 transitionmetal-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.