Development of new photocatalytic ring-opening reaction of cyclopropanols Anastasiya Krech, Dzmitry Kananovich, Maksim Ošeka Tallinn University of Technology, Estonia Cyclopropanols are useful three-carbon building blocks for organic synthesis. Oxidative activation and radical ring opening of cyclopropanols leading to the formation of β-keto radicals can be achieved using transition metal catalysts, stoichiometric oxidants and photoredox catalysts. 1 Herein, we report a photocatalyzed reaction of cyclopropyl alcohol and electron-deficient olefine using tetrabutylammonium decatungstate (TBADT) as a catalyst. In contrast to the typical behavior of TBADT, we believe that the reaction follows single-electron transfer mechanism and is based on simultaneous oxidation of cyclopropanol and reduction of alkene. 2 Addition of an external oxidant accelerates the reaction and activates otherwise inert substrates. The reaction can be successfully scaled-up under the continuous-flow conditions.
References 1. T. R. McDonald, L. Reginald Mills, M. S. West, S. A. L. Rousseaux Chem. Rev. 2021 , 121 , 3. 2. a) S. Montanaro, D. Ravelli, D. Merli, M. Fagnoni, A. Albini Org. Lett. 2012 , 14 , 4218 b) L. Capado, L. Buzzetti, D. Merli, M. Fagnoni, D. Ravelli J. Org. Chem. 2016 , 81 , 7102.
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