Photoinduced decarboxylative benzylation of phthalimide triplets with phenyl acetates: a mechanistic study

The Journal of Physical Chemistry. a
Klaus-Dieter WarzechaAxel G Griesbeck

Abstract

The photodecarboxylative benzylation of N-alkyl, N-arylalkyl, and N-aryl phthalimides with arylacetic acids in aqueous solution proceeds via electron transfer from the arylalkanoate to the excited triplet state of the phthalimide, either formed directly or upon sensitization with acetone. The rate constant for triplet quenching of N-methylphthalimide is k(q) < 10(7) M(-1) s(-1) for 2-phenylacetic acid and k(q) = (1-3) x 10(9) M(-1) s(-1) for its mono-, di- and trimethoxy-substituted derivatives, suggesting a change of the mechanism for the primary oxidation step from a Photo-Kolbe type reaction yielding an acyloxy radical to a pseudo-Photo-Kolbe process involving the formation of resonance-stabilized zwitterion radicals as intermediates.

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Citations

Apr 24, 2010·Chemical Communications : Chem Comm·Alberto SoldevillaAxel Griesbeck
Jan 1, 2007·Acta Crystallographica. Section E, Structure Reports Online·Zhou JiangJin-Ling Huang
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Marcos Flores-AlamoJorge Morgado
Sep 23, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Julia Pérez-PrietoMaria C Morant-Miñana
Aug 21, 2012·Acta Crystallographica. Section E, Structure Reports Online·Hiroki Takahashi
Jan 20, 2015·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Gabriela Oksdath-MansillaAlicia B Peñéñory
Oct 8, 2013·Acta Crystallographica. Section E, Structure Reports Online·Noemi VilaCarmen Terán
Nov 3, 2016·Organic & Biomolecular Chemistry·Ping LiuPeipei Sun
Sep 15, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Robert LechnerBurkhard König
Jan 27, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Margareta HorvatNikola Basarić
Aug 23, 2018·Chemistry : a European Journal·Sarah E BorderJovica D Badjić
Oct 31, 2009·The Journal of Organic Chemistry·Margareta HorvatNikola Basarić
Jan 12, 2007·The Journal of Physical Chemistry. a·Masanori SakamotoTetsuro Majima
Dec 8, 2017·Journal of the American Chemical Society·Sarah E BorderJovica D Badjić

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