Catalyst Design Team

To realize a sustainable society, the role that chemical technology plays is vital. Our research focuses on the development of green synthetic processes by utilizing catalysis as a core technology for minimizing wastes, maximizing energy efficiency in chemical processes, and shifting raw materials to renewable resources.

Team Leader, Dr. Jun-Chul Choi(Ph.D.)

Theme

  • Development of Novel Immobilized Catalysts
  • Synergistic Hybrid Catalysts
  • Magnetically Recoverable Osmium Catalysts
  • Efficient Synthesis via Nanoporous Catalysts

Development of Novel Immobilized Catalysts

We have developed a tripodal linker unit that enables firm immobilization of molecular catalysts on silica. The silica-immobilized amino-palladium complex catalyst via the tripodal linker is effective for preventing metal leaching into the product after the Suzuki coupling reaction.

Synergistic Hybrid Catalysts

The catalytic activity of onium salts towards cyclic carbonate synthesis from propylene oxide and CO2 is enormously enhanced by their immobilization onto silica that itself has no catalytic activity.

Magnetically Recoverable Osmium Catalysts

We have developed magnetically recoverable osmium catalysts. By employing 2 mol% of the magnetic osmium catalyst, the dihydroxylation reaction proceeds smoothly to provide the vicinal diol. The catalyst is readily recovered by use of an external magnet, and is reused repeatedly.

Efficient Synthesis via Nanoporous Catalysts

We have found that mesoporous alumino-silicates (Al-MCM-41) exhibit much higher catalytic activities than amorphous silica-alumina or zeolites for several important reactions in organic synthesis, including cyanosilylation and Mukaiyama aldol reaction.

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Members

Position Name Email(*)
Leader Jun-chul CHOI junchul.choi
Senior researcher Toshikazu TAKAHASHI takahashi.toshikazu
Senior researcher Ken-ichi FUJITA k.fujita
Senior researcher Norihisa FUKAYA n.fukaya
Post doctoral researcher Qiao ZHANG
Technical staff Toshio HORIKOSHI
Technical staff Akira FUJII
Technical staff Vlasenkova Liudmila
Assistant Etsuko HORIIKE
Graduate student (D3), RA Haoyu YUAN
Graduate student (M2), RA Yuki OKUDA
Graduate student (M2), RA Kohei HATAKEYAMA
Graduate student (M1), RA Keisuke FUKAYA
Graduate student (M1) Xiaotao LIN
Undergraduate student (B4) Yuto SEO

*Please add “@aist.go.jp” after each local part.

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Results

K. Fujii, Akira, J.-C. Choi, K. Fujita
Synthesis of magnetically recoverable imidazolium hydrogen carbonate and its application as an N-heterocyclic carbene catalyst to cyanosilylation of aldehydes and ketones
Tetrahedron Lett., 58, 1515-1518 (2017).

Q. Zhang, H.-Y. Yuan, N. Fukaya, H. Yasuda, J.-C. Choi
A simple zinc catalyst for carbamate synthesis directly from CO2
ChemSusChem, 10, 1501-1508 (2017).

N. Fukaya, S.J. Choi, T. Horikoshi, S. Kataoka, A. Endo, H. Kumai, M. Hasegawa, K. Sato, J.-C. Choi
Direct synthesis of tetraalkoxysilanes from silica and alcohols
New J. Chem., 41, 2224-2226 (2017).

H.-Y. Yuan, J.-C. Choi, S. Onozawa, N. Fukaya, S.J. Choi, H. Yasuda, T. Sakakura
The direct synthesis of N-phenylcarbamates from CO2, aniline, and dibutyltin dialkoxide
J. CO2 Util., 16, 282-286 (2016).

S. Yamane, T. Takahashi, Y. Suzuki, T. Miyadera, T. Koganezawa, K. Arai, Y. Akiyama, M. Chikamatsu, Y. Yoshida, H. Suda, J. Mizukado
Thermal stabilization of organic photovoltaic cells using [6,6]-phenyl C61-butyric acid methyl ester analogs: Effects of alkyl substituents on the nanostructures of bulk heterojunction films and their stabilities
Synthetic Met., 221, 61-66 (2016).

S. Banerjee, S. Kataoka, T. Takahashi, Y. Kamimura, K. Suzuki, K. Sato, A. Endo
Controlled formation of ordered coordination polymeric networks using silsesquioxane building blocks
Dalton T., 45, 17082-17086 (2016).

N. Fukaya, S.J. Choi, T. Horikoshi, H. Kumai, M. Hasegawa, H. Yasuda, K. Sato, J.-C. Choi
Synthesis of tetramethoxysilane from silica and methanol using carbon dioxide and an organic dehydrating reagent
Chem. Lett., 45, 828-830 (2016).

N. Fukaya, T. Miyaji, S. Onozawa, S.J. Choi, M. Ueda, Y. Takagi, J.-C. Choi, T. Sakakura, H. Yasuda
Application of tripodal linker units to immobilized diphenylphosphine palladium complex catalysts for Suzuki-Miyaura coupling reactions of aryl bromide: Effect of immobilization method of phosphine ligand on catalytic performance
J. Jpn. Petrol. Inst., 59, 118-125 (2016).

K. Fujita, A. Fujii, J. Sato, H. Yasuda
Magnetically Recoverable N-Heterocyclic Carbene-Gold(I) Catalyst for Hydroamination of Terminal Alkynes
Synlett, 27, 1941-1944 (2016).

K. Fujita, H. Hattori
Synthesis of dendrimers with a bidentate phosphine core ligand having carboxy groups at the peripheral layer and their application to aqueous media cross-coupling reactions
Chem. Pharm. Bull., 64, 1067-1072 (2016).

K. Fujita, J. Sato, A. Fujii, S. Onozawa, H. Yasuda
A carboxylative cyclization of propargylic amines with carbon dioxide catalyzed by the N-heterocyclic carbene 1,3-Di-tert-butylimidazol-2-ylidene (ItBu)
Asian J. Org. Chem., 5, 828-833 (2016).

K. Fujita, A. Fujii, J. Sato, S. Onozawa, H. Yasuda
Synthesis of 2-oxazolidinone by N-heterocyclic carbene-catalyzed carboxylative cyclization of propargylic amine with CO2
Tetrahedron let., 57, 1282-1284 (2016).

K. Fujita, H. Hattori
Suzuki-Miyaura reaction catalyzed by a dendritic phosphine-palladium complex
Tetrahedron, 72, 1485-1492 (2016).

K. Fujita, K. Inoue, J. Sato, T. Tsuchimoto, H. Yasuda
Carboxylative cyclization of propargylic amines with CO2 catalyzed by dendritic N-heterocyclic carbene-gold(I) complexes
Tetrahedron, 72, 1205-1212 (2016).

K. Fujita, J. Sato, H. Yasuda
Tautomerization of 5-alkylidene-2-oxazolidinone to 2-oxazolone by use of an N-heterocyclic carbene catalyst
Synlett, 26, 1106-1110 (2015).

S. Yamane, J. Mizukado, T. Takahashi, Y. Suzuki, M. Sakurai, H. Hagihara, H. Suda
Fulleropyrrolidine derivatives with benzophenone moiety as electron acceptors in thermally stable organic photovoltaic devices
Chem. Lett., 44, 527-529 (2015).

S. Kataoka, S. Banerjee, A. Kawai, Y. Kamimura, J.-C. Choi, T. Kodaira, K. Sato, A. Endo
Layered hybrid perovskites with micropores created by alkylammonium functional silsesquioxane interlayers
J. Am. Chem. Soc., 137, 4158-4163 (2015).

K. Fujita, J. Sato, K. Inoue, T. Tsuchimoto, H. Yasuda
Aqueous media carboxylative cyclization of propargylic amines with CO2 catalyzed by amphiphilic dendritic N-heterocyclic carbene-gold(I) complexes
Tetrahedron Lett., 55, 3013-3016 (2014).

J. Blanchard, J.-M. Krafft, C. Dupont, C. Sayag, T. Takahashi, H. Yasuda
On the influence of water traces on the acidity measurement of amorphous aluminosilicates
Catal. Today, 226, 89-96 (2014).

N. Fukaya, S. Onozawa, M. Ueda, T. Miyaji, Y. Takagi, T. Sakakura, H. Yasuda
Palladium phosphine complex catalysts immobilized on silica via a tripodal linker unit for the Suzuki-Miyaura coupling reactions of arylchlorides
J. Mol. Catal. A: Chem., 385, 7-12 (2014).

J.-C. Choi, K. Shiraishi, Y. Takenaka, H. Yasuda, T. Sakakura
Synthesis and reactivity of five-membered palladalactones from arylallenes and carbon dioxide: Relevance to catalytic lactone synthesis
Organometallics, 32, 3411-3414 (2013).

K. Fujita, S. Umeki, H. Yasuda
Magnetically recoverable osmium catalysts with osmium-diolate esters for dihydroxylation of olefins
Synlett, 947-950 (2013).

S. Onozawa, T. Miyaji, N. Fukaya, M. Yoshinaga, M. Ueda, Y. Takagi, H. Yasuda
A bidentate ligand immobilized on silica via a tripodal linker unit: Preparation and application to Suzuki-Miyaura coupling
Chem. Lett., 42, 275-277 (2013).

Q.-W. Song, L.-N. He, J.-Q. Wang, H. Yasuda. T. Sakakura
Catalytic fixation of CO2 to cyclic carbonates by phosphonium chlorides immobilized on fluorous polymer
Green Chem., 15, 110-115 (2013).

K. Fujita, K. Inoue, T. Tsuchimoto, H. Yasuda
Homogeneous dihydroxylation of olefins catalyzed by OsO42– immobilized on a dendritic backbone with a tertiary nitrogen at its core position
Chem. Pharm. Bull., 60, 1594-1598 (2012).

S. Kataoka, Y. Takeuchi, A, Harada, T. Takagi, Y. Takenaka, N. Fukaya, H. Yasuda, T. Ohmori, A. Endo
Microreactor containing platinum nanoparticles for nitrobenzene hydrogenation
Appl. Catal. A, 427-428, 119-124 (2012).

Y. Takenaka, T. Kiyosu, G. Mori, J.-C. Choi, N. Fukaya, T. Sakakura, H. Yasuda
Synthesis of cyclic sulfites from epoxides and sulfur dioxide with silica-immobilized homogeneous catalysts
ChemSusChem, 5, 194-199 (2012).

J.-C. Choi, K. Kohno, M. Otsuka, H. Yasuda, T. Sakakura
Synthesis of a rhodium(III) diethyl μ-carbonato complex in the reaction of CO2, H2O, and ethylene
Organometallics, 30, 6060-6062 (2011).

N. Fukaya, M. Ueda, S. Onozawa, K. K. Bando, T. Miyaji, Y. Takagi, T. Sakakura, H. Yasuda
Palladium complex catalysts immobilized on silica via a tripodal linker unit with amino groups: Preparation, characterization, and application to the Suzuki–Miyaura coupling
J. Mol. Catal. A, 342-343, 58-66 (2011).

K. Fujita, S. Umeki, M. Yamazaki, T. Ainoya, T. Tsuchimoto, H. Yasuda
Magnetically recoverable osmium catalysts for dihydroxylation of olefins
Tetrahedron Lett., 52, 3137-3140 (2011).

S. Onozawa, N. Fukaya, K. Saitou, T. Sakakura, H. Yasuda
PEG modification effect of silica on the Suzuki-Miyaura coupling reaction using silica-immobilized palladium catalysts
Catal. Lett., 141, 866-871 (2011).

T. Miyaji, S. Onozawa, N. Fukaya, M. Ueda, Y. Takagi, T. Sakakura, H. Yasuda
Diphenylphosphino functionalization of mesoporous silica using tripodal linker units
J. Organomet. Chem., 696, 1565-1569 (2011).

Y. Takenaka, T. Kiyosu, G. Mori, J.-C. Choi, T. Sakakura, H. Yasuda
Selective hydrogenation of nitroalkane to N-alkyl hydroxylamine over supported palladium catalysts Catal. Today, 164, 580-584 (2011).

N. Fukaya, S. Onozawa, M. Ueda, T. Miyaji, Y. Takagi, T. Sakakura, H. Yasuda
Application of tripodal linker units to immobilized rhodium complex catalysts for asymmetric hydrogenation
Chem. Lett., 40, 212-214 (2011).N. Fukaya, H. Yamashita, H. Haga, T. Tsuchimoto, S. Onozawa, T. Sakakura, H. Yasuda
Microwave-assisted organic functionalization of silica surfaces: Effect of selectively heating silylating agents
J. Organomet. Chem., 696, 825-828 (2011).

N. Fukaya, H. Haga, T. Tsuchimoto, S. Onozawa, T. Sakakura, H. Yasuda
Organic functionalization of the surface of silica with arylsilanes. A new method for synthesizing organic–inorganic hybrid materials
J. Organomet. Chem., 695, 2540-2542 (2010).

Y. Takenaka, T. Kiyosu, J.-C. Choi, T. Sakakura, H. Yasuda
Selective synthesis of N-alkyl hydroxylamines by hydrogenation of nitroalkanes using supported palladium catalysts
ChemSusChem, 3, 1166-1168 (2010).

K. Fujita, M. Yamazaki, T. Ainoya, T. Tsuchimoto, H. Yasuda
A recyclable dendritic osmium catalyst for homogeneous dihydroxylation of olefins
Tetrahedron, 66, 8536-8543 (2010).

N. Fukaya, S. Onozawa, M. Ueda, K. Saitou, Y. Takagi, T. Sakakura, H. Yasuda
Design and synthesis of new linker units for covalently immobilizing organic functional molecules
Chem. Lett., 39, 402-403 (2010).

K. Iwanami, H. Seo, J.-C. Choi, T. Sakakura, H. Yasuda
Al-MCM-41 catalyzed three-component Strecker-type synthesis of α-aminonitriles
Tetrahedron, 66, 1898-1901 (2010).

K. Fujita, T. Ainoya, T. Tsuchimoto, H. Yasuda
Homogeneous dihydroxylation of olefins catalyzed by a recyclable OsO42- core dendrimer
Tetrahedron Lett., 51, 808-810 (2010).

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