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Alcohol Oxidation Catalysts

  • School of Engineering/Graduate School of Engineering
  • Department of Molecular and Macromolecular Chemistry
  • Research Group of Molecular Chemistry
  • (Laboratory of Catalysis in Organic Synthesis)

Kazuaki Ishihara [Professor]

http://www.ishihara-lab.net/english/

  • School of Engineering/Graduate School of Engineering
  • Department of Molecular and Macromolecular Chemistry
  • Research Group of Molecular Chemistry
  • (Laboratory of Catalysis in Organic Synthesis)

Muhammet Uyanik [Assistant Professor]

Outline of Seeds

Alcohols are selectively oxidized to aldehydes, ketones, or carboxylic acids in the presence of catalytic amounts of 2-iodobenzenesulfonic acid and stoiciometric amounts of Oxone. 2-Iodobenzenesulfonic acid is oxidized to 2-iodoxybenzenesulfonic acid (IBS) in situ with Oxone. IBS is a catalytic species. Selective oxidation can be controlled by using suitable amounts of Oxone and solvents.

Novelty and originality of this research

IBS (0.05-5 mol%) is much more efficient than IBX (10-20 mol%). The selective oxidation is possible by using IBS. The IBS-oxidation is environmentally benign.

Application and research area for Industry collaboration

Pharmaceuticals and their intermediates in synthetic process

Key Takeaway

Our interest is rational design of high performance catalysts based on acid-base combination chemistry.

Keywords

Synthetic organic chemistry, biomimetic chemistry, green chemistry, process chemistry, organometallic chemistry, chemistry of catalysis, acid-base combination chemistry, chemical catalysts, artificial catalysts, asymmetric synthesis, stereoselective syntheisis, pharmaceuticals, natural products, bioactive compounds, functional organic materials

Technologies

  • Synthetic technology of organic compounds
  • Experiments into a glove box
  • Structural analysis of organic compounds

Equipment

  • NMR, IR, Polarimeter, HPLC, Recycling preparative HPLC, GC, GCMS, GPC, X-ray diffraction instrument, globe box, Ultrasound, Microwave, Freezer, Karl Fischer Moisture Titrator, High vaccum line, Pararel Synthsizer, Melting-point instrument, High-pressure instrument

Monographs, Papers and Articles

  • “2-Iodoxybenzenesulfonic acid (IBS) as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids and enones with Oxone®,” Muhammet Uyanik, Matsujiro Akakura, Kazuaki Ishihara J. Am. Chem. Soc. 2009, 131(1), 251–262.
  • "“IBS-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxone®,” Muhammet Uyanik, Ryota Fukatsu, Kazuaki Ishihara, Org. Lett. 2009, 11(15), 3470–3473. "
  • "“2-Iodoxy-5-methylbenzenesulfonic acid-catalyzed selective oxidation of 4-bromobenzyl alcohol to 4-bromobenzaldehyde or 4-bromobenzoic acid with oxone,” Muhammet Uyanik, Kazuaki Ishihara, Org. Synth. 2012, 89, 105–114. "
  • “IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®,” Muhammet Uyanik, Tatsuya Mutsuga, Kazuaki Ishihara, Molecules 2012, 17(7), 8604–8616.