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Transition-Metal-Free Arylations via Photogenerated Triplet 4-Alkyl and 4-Trimethylsilylphenyl Cations

Authors: 
Hisham Qrareya, Carlotta Raviola, Stefano Protti, Maurizio Fagnoni, and Angelo Albini.
Journal Name: 
The Journal of Organic Chemistry (JOC).
Volume: 
78
Issue: 
12
Pages From: 
6016
To: 
6024
Date: 
Monday, May 20, 2013
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.