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Green/sustainable organic synthesis based on H2O, hydrogen, biomass-feedstock, light, and CO2

  • Institute for Advanced Research
  • Graduate School of Science
  • Department of Chemistry
  • (The NOYORI Laboratory)

Susumu Saito [Associate Professor]

http://noy.chem.nagoya-u.ac.jp/Noy_e/Top/Top.html

Outline of Seeds

CO2, carboxylic acids, peptides, sugars, and lipids are ubiquitous and richly available from bio-renewable sources of carbon. Carbon-neutral alternatives to fossil fuels present a critical challenge for the scientific community in producing a sustainable society, and thus, sourced from biomass and/or as the products of syntheses from CO2, these are a potential renewable resource. We are developing competent molecular and semiconductor photo- and thermal-catalysis that potentially have a number of applications in materials sciences and organic synthesis to achieve these goals.

Novelty and originality of this research

Photo-catalysis and molecular catalysis have been underestimated for the chemical transformation of thermodynamically stable and kitetically inert compunds such as CO2 and biomass-derived feedstock. However, we have demonstrated that methodologies we developed are very useful for such transformations which are otherwise very diffcult to achieve using preceding methods.

Application and research area for Industry collaboration

Hydrogenation/dehydrogenation, as well as hydration/dehydration are useful tools for chemcial transformation of CO2 and biomass-derived feedstock. For instance, Hydrogenation of carboxylic acids to yield alcohols produces water as the only byproduct, and is a possible next-generation, sustainable method for large-scale production of alternative energy carriers/platform chemicals. Dehydrogenation of alcohols can make a rapid access to pharmaceutically important substances including Donepezil and Lipitor. A molecular library of nonstandard peptides may be also accessible through hydrogenation of amides and carboxylic acids, as well as N-alkylation using alcohols.

Key Takeaway

Elements and bonds - by eleborating special alignment of these basic composites of molecules that consitute molecular and photo catalysts, unprecdented reactivity and selectivity can be obtained for chemical transformation of CO2 and biomass-derived feedstock.

Keywords

Organic synthesis, molecular catalysis, photo-catalysis, organometallics, hydrogen transfer, hydrogenation, CO2, green/sustainable synthesis

Technologies

  • Organic synthesis, photocatalyst synthesis, Synthesis/pyrification of thermodynamically unstable compounds
  • Identification of organic compounds and their optical purities using NMR, ESI-Mass, and optical rotation
  • Gas and liguid chromatography for purification and analysis of organic compounds
  • X-ray single crystal analysis

Equipment

  • NMR, X-ray diffraction, globe box (shared), GS-MS, analytical and preparative HPLC, automated Hydrogenation

Patents

  • PCT/JP2014/55510 Synthesis of ligands, metal complexes bearing the ligands, and reactions using the metal complexes

Monographs, Papers and Articles

  • “Catalytic hydrogenation of unactivated amides enabled by hydrogenation of catalyst precursor” Takashi Miura, Ingmar E. Held, Shunsuke Oishi, Masayuki Naruto, Susumu Saito. Tetrahedron Letters 54, 2674–2678 (2013).
  • “The dual role of ruthenium and alkali base catalysts in enabling a conceptually new shortcut to N-unsubstituted pyrroles via unmasked α-amino aldehydes” Kazuki Iida, Takashi Miura, Junki Ando, Susumu Saito. Org. Lett., 15 (7), 1436–1439 (2013).
  • “Synthesis of propylene from renewable allyl alcohol by photocatalytic transfer hydrogenolysis” Joaquim Caner, Zijun Liu, Yuki Takada, Akihiko Kudo, Hiroshi Naka, Susumu Saito. Catal. Sci. Technol. 4(11), 4093–4098 (2014).
  • “Catalytic fluoride triggers dehydrative oxazolidinone synthesis from CO2” Yuki Takada, Siong Wan Foo, Yusuke Yamazaki, Susumu Saito. RSC Adv., 4, 50851-50857 (2014).