Transition-metal-free arylations via photogenerated triplet 4-alkyl- and 4-trimethylsilylphenyl cations

Hisham Qrareya; Carlotta Raviola; Stefano Protti; Maurizio Fagnoni; Angelo Albini

doi:10.1021/jo4007046

Transition-metal-free arylations via photogenerated triplet 4-alkyl- and 4-trimethylsilylphenyl cations

J Org Chem. 2013 Jun 21;78(12):6016-24. doi: 10.1021/jo4007046. Epub 2013 May 31.

Authors

Hisham Qrareya¹, Carlotta Raviola, Stefano Protti, Maurizio Fagnoni, Angelo Albini

Affiliation

¹ PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy.

PMID: 23688128
DOI: 10.1021/jo4007046

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 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.