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.