Photoarylation/alkylation of bromonaphthols

The Journal of Organic Chemistry
Luca PretaliMauro Freccero

Abstract

The photochemistry of 6-bromo-2-naphthols has been studied in acetonitrile, aqueous acetonitrile, and isopropyl alcohol in the absence and in the presence of triethylamine by product distribution analysis, laser flash photolysis (LFP), fluorescence, phosphorescence, electrochemical measurements, and DFT calculations. Hydrobromic acid loss in the presence of Et(3)N occurs from the triplet state of 6-bromo-2-naphthol, generating an electrophilic carbene intermediate, which has been successfully trapped by oxygen, allyltrimethylsilane, 2,3-dimethylbut-2-ene, pyrrole, acrylonitrile, 1,4-dimethoxybenzene, and also pyridine. The generation and the reactivity of a triplet carbene intermediate has been supported by LFP, with the detection of 2,6-naphthoquinone-O-oxide (530 < lambda < 650 nm) in the presence of O(2). The electrophilic diradical character of the carbene has been supported by DFT calculations, using the B3LYP, PBE0, and MPWB1K functionals, with the 6-31+G(d,p) basis set and PCM solvation model.

References

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Citations

May 24, 2017·The Journal of Organic Chemistry·Đani ŠkalameraNikola Basarić
Apr 25, 2014·The Journal of Organic Chemistry·Đani ŠkalameraNikola Basarić
Oct 28, 2015·Chemical Communications : Chem Comm·Anjan DasKenneth Hanson
Mar 2, 2019·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Matija SambolNikola Basarić
Apr 7, 2010·The Journal of Organic Chemistry·Daniela VergaMauro Freccero
Nov 12, 2010·Journal of the American Chemical Society·Jillian L DempseyHarry B Gray
Mar 10, 2011·The Journal of Organic Chemistry·Daniela VergaMauro Freccero
Apr 27, 2012·The Journal of Organic Chemistry·Jelena VeljkovićNikola Basarić

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