Schmaderer, Harald and Hilgers, Petra and Lechner, Robert and König, Burkhard (2009) Photooxidation of Benzyl Alcohols with Immobilized Flavins. Advanced Synthesis & Catalysis 351, pp. 163-174.
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Benzyl alcohols are oxidized cleanly and efficiently to the corresponding aldehydes under irradiation using flavin photocatalysts and aerial oxygen as the terminal oxidant in homogeneous aqueous solution. Turnover frequencies (TOF) of more than 800 h⁻¹ and turnover numbers (TON) of up to 68
were obtained. Several flavin photocatalysts with fluorinated or hydrophobic aliphatic chains were immobilized on solid supports like fluorous silica gel, reversed phase silica gel or entrapped in polyethylene pellets. The catalytic efficiency of the heterogeneous photocatalysts was studied for the oxidation of different benzyl alcohols in water and compared to the analogous homogeneous reactions. Removal of the
heterogeneous photocatalyst stops the reaction conversion
immediately, which shows that the immobilized flavin is the catalytically active species. The immobilized catalysts are stable, retain their reactivity if compared to the corresponding homogeneous systems and are easily removed from the reaction mixture and reused. TOF of up to 26 h⁻¹, TON of 280
and up to 3 reaction cycles without loss of activity are possible with the heterogeneous flavin photocatalysts.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König|
|Projects:||GRK 640 Sensory photoreceptors in natural and artificial systems|
|Keywords:||catalyst recycling; flavins; fluorous chemistry; immobilization; photooxidation; redox chemistry|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||05 Jun 2009 14:31|
|Last Modified:||27 Aug 2012 13:02|