ITO, Hajime

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ITO, Hajime
Principal Investigator, Vice Director
Hokkaido University
Research Areas
Organic Synthetic Chemistry, Organoelement Chemistry, Mechanochemistry
Related Website

hajito atmark

ITO, Hajime Group
Principal Investigator
  • thumbnail image
    ITO, Hajime
Faculty Members
Postdoctoral Fellows
Research Collaborators
  • HU, Anqi

About the Research

Research Theme

Development of new reactions of small molecules with various elements


Development of New Reactions, Mechano-Responsive Materials, Mechanochemical Synthesis
Research Outline

Our research group has three main topics. The first is the development of new reactions for organic synthesis using copper, boron, and other organo-metallic compounds. The second is the development of new materials that show interesting optical properties in response to mechanical stress such as grinding. And the third topic is mechano-chemical synthesis. This solvent-free approach promises to be more efficient and environmentally friendly than current light-activated reaction mechanisms.

Calculations constitute an increasingly important technology for the development of new chemical reactions, because experimental chemists have so far relied mainly on experimental screening or serendipity. But computational methods, especially the AFIR method, can predict new reactions and thus guide our search.

For details on MANABIYA course topics, please follow this link. To learn more about MANABIYA in general, please click here.

The Researcher’s Perspective

Whenever we come across an interesting, new phenomenon, we develop new projects. This is to the benefit of our students, who within their studies can successfully complete sometimes several projects. I am very lucky to be surrounded by excellent colleagues, so we are discovering many exciting things every day!

Representative Research Achievements

  • Reversible Mechanochromic Luminescence of (C6F5Au)2(μ-1,4-diisocyanobenzene)
    H. Ito, T. Saito, N. Oshima, N. Kitamura, S. Ishizaka, Y. Hinatsu, M. Wakeshima, M. Kato, K. Tsuge, M. Sawamura, J. Am. Chem. Soc., 2008, 130, 10044–10045
    DOI : 10.1021/ja8019356
  • A Screening Approach for the Discovery of Mechanochromic Gold(I) Isocyanide Complexes with Crystal-to-Crystal Phase Transitions
    T. Seki, Y. Takamatsu, H. Ito, J. Am. Chem. Soc., 2016, 138, 6252–6260
    DOI : 10.1021/jacs.6b02409
  • Mechanochromic Luminescence Based on Crystal-to-Crystal Transformation Mediated by a Transient Amorphous State
    S. Yagai, T. Seki, H. Aonuma, K. Kawaguchi, T. Karatsu, T. Okura, A. Sakon, H. Uekusa, H. Ito, Chem. Mater., 2016, 28, 234–241
    DOI : 10.1021/acs.chemmater.5b03932
  • Boration of an α,β-enone Using a Diboron Promoted by a Copper(I)-Phosphine Mixture Catalyst
    H. Ito, H. Yamanaka, J. Tateiwa, A. Hosomi, Tetrahedron Lett., 2000, 41, 6821–6825
    DOI : 10.1021/om800946k
  • Copper-Catalyzed Enantioselective Substitution of Allylic Carbonates with Diboron: An Efficient Route to Optically Active alpha-Chiral Allylboronates
    H. Ito, S. Ito, Y. Sasaki, K. Matsuura, M. Sawamura, J. Am. Chem. Soc., 2007, 129, 14856–14857
    DOI : 10.1021/ja076634o

Related Research



  • Synthesis of Chiral N-Heterocyclic Allylboronates via the Enantioselective Borylative Dearomatization of Pyrroles
    K. Hayama, R. Kojima, K. Kubota, H. Ito, Org. Lett., 2020, 22, 739-744
    DOI: 10.1021/acs.orglett.9b04581
  • Aurophilicity-Mediated Construction of Emissive Porous Molecular Crystals as Versatile Hosts for Liquid and Solid Guests
    T. Seki, K. Ida, H. Sato, S. Aono, S. Sakaki, H. Ito, Chem. Eur. J., 2020, 26, 735-744
    DOI: 10.1002/chem.201904597
  • Synthesis and Tunable Optical Properties of C,N-Chelated Borate Luminophores Derived from Potassium Acyltrifluoroborates
    J. Taguchi, S. Matsuura, T. Seki, H. Ito, Chem. Eur. J., 2020, 26, 2450-2455
    DOI: 10.1002/chem.201904983
  • Air- and Moisture-Stable Xantphos-Ligated Palladium Dialkyl Complex as a Precatalyst for Cross-Coupling Reactions
    R. Takahashi, K. Kubota, H. Ito, Chem. Commun., 2020, 56, 407-410
    DOI: 10.1039/c9cc06946a


  • Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives
    S. Akiyama, K. Kubota, MS. Mikus, PHS. Paioti, F. Romiti, QH. Liu, YB. Zhou, AH. Hoveyda, H. Ito, Angew. Chem., Int. Ed., 2019, 58, 11998-12003
    DOI: 10.1002/anie.201906283
  • Dependence of Absorption and Emission Spectra on Polymorphs of Gold(I) Isocyanide Complexes: Theoretical Study with QM/MM Approach
    S. Aono, T. Seki, H. Ito, S. Sakaki, J. Phys. Chem. C, 2019, 123, 4773-4794
    DOI: 10.1021/acs.jpcc.8b10602
  • Near-IR Luminescent YbIII Coordination Polymers Composed of Pyrene Derivatives for Thermostable Oxygen Sensors
    Y. Hasegawa, T. Matsui, Y. Kitagawa, T. Nakanishi, T. Seki, H. Ito, Y. Nakasaka, T. Masuda, K. Fushimi, Chem. Eur. J., 2019, 25, 12308-12315
    DOI: 10.1002/chem.201902583
  • Microphase Separation of Carbohydrate-Based Star-Block Copolymers with Sub-10 nm Periodicity
    T. Isono, N. Kawakami, K. Watanabe, K. Yoshida, I. Otsuka, H. Mamiya, H. Ito, T. Yamamoto, K. Tajima, R. Borsali, T. Satoh, Polym. Chem., 2019, 10, 1119-1129
    DOI: 10.1039/c8py01745j
  • Copper(I)-Catalyzed Enantioconvergent Borylation of Racemic Benzyl Chlorides Enabled by Quadrant-by-Quadrant Structure Modification of Chiral Bisphosphine Ligands
    H. Iwamoto, K. Endo, Y. Ozawa, Y. Watanabe, K. Kubota, T. Imamoto, H. Ito, Angew. Chem., Int. Ed., 2019, 58, 11112-11117
    DOI: 10.1002/anie.201906011
  • Anisotropic Thermal Expansion as the Source of Macroscopic and Molecular Scale Motion in Phosphorescent Amphidynamic Crystals
    M. Jin, S. Yamamoto, T. Seki, H. Ito, MA. Garcia-Garibay, Angew. Chem., Int. Ed., 2019, 58, 18003-18010
    DOI: 10.1002/anie.201909048
  • Redox Reactions of Small Organic Molecules Using Ball Milling and Piezoelectric Materials
    K. Kubota, YD. Pang, A. Miura, H. Ito, Science, 2019, 366, 1500-1504
    DOI: 10.1126/science.aay8224
  • Olefin-Accelerated Solid-State C-N Cross-Coupling Reactions Using Mechanochemistry
    K. Kubota, T. Seo, K. Koide, Y. Hasegawa, H. Ito, Nat. Commun., 2019, 10,
    DOI: 10.1038/s41467-018-08017-9
  • Mechanochemistry Allows Carrying out Sensitive Organometallic Reactions in Air: Glove-Box-and-Schlenk-Line-Free Synthesis of Oxidative Addition Complexes from Aryl Halides and Palladium(0)
    K. Kubota, R. Takahashi, H. Ito, Chem. Sci., 2019, 10, 5837-5842
    DOI: 10.1039/c9sc01711a
  • Synthesis of 2-Alkyl-2-Boryl-Substituted-Tetrahydrofurans via Copper(I)-Catalysed Borylative Cyclization of Aliphatic Ketones
    K. Kubota, M. Uesugi, S. Osaki, H. Ito, Org. Biomol. Chem., 2019, 17, 5680-5683
    DOI: 10.1039/c9ob00962k
  • Iridium(I)-Catalyzed C-H Borylation in Air by Using Mechanochemistry
    YD. Pang, T. Ishiyama, K. Kubota, H. Ito, Chem. Eur. J., 2019, 25, 4654-4659
    DOI: 10.1002/chem.201900685
  • Luminescent Mechanochromism of Gold N-Heterocyclic Carbene Complexes with Hypso- and Bathochromic Spectral Shifts
    T. Seki, K. Kashiyama, H. Ito, Dalton Trans., 2019, 48, 7105-7109
    DOI: 10.1039/c9dt00566h
  • Anisotropic Strain Release in a Thermosalient Crystal: Correlation Between the Microscopic Orientation of Molecular Rearrangements and the Macroscopic Mechanical Motion
    T. Seki, T. Mashimo, H. Ito, Chem. Sci., 2019, 10, 4185-4191
    DOI: 10.1039/c8sc05563g
  • Solid-State Suzuki-Miyaura Cross-Coupling Reactions: Olefin-Accelerated C-C Coupling Using Mechanochemistry
    T. Seo, T. Ishiyama, K. Kubota, H. Ito, Chem. Sci., 2019, 10, 8202-8210
    DOI: 10.1039/c9sc02185j
  • Concise Synthesis of Potassium Acyltrifluoroborates from Aldehydes Through Copper(I)-Catalyzed Borylation/Oxidation
    J. Taguchi, T. Takeuchi, R. Takahashi, F. Masero, H. Ito, Angew. Chem., Int. Ed., 2019, 58, 7299-7303
    DOI: 10.1002/anie.201901748


  • Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino-Acid Acylboronate
    J. Taguchi, T. Ikeda, R. Takahashi, I. Sasaki, Y. Ogasawara, T. Dairi, N. Kato, Y. Yamamoto, JW. Bode, H. Ito, Angew. Chem., Int. Ed., 2017, 56, 13847-13851
    DOI: 10.1002/anie.201707933


  • Cationic Ir/Me-BIPAM-Catalyzed Asymmetric Intramolecular Direct Hydroarylation of α-Keto Amides
    T. Shirai, H. Ito, Y. Yamamoto, Angew. Chem., Int. Ed., 2014, 53, 2658-2661
    DOI: 10.1002/anie.201400147


  • Tetrabutylammonium 2-Pyridyltriolborate Salts for Suzuki-Miyaura Cross-Coupling Reactions with Aryl Chlorides
    S. Sakashita, M. Takizawa, J. Sugai, H. Ito, Y. Yamamoto, Org. Lett., 2013, 15, 4308-4311
    DOI: 10.1021/ol402268g
  • Cross-Coupling Reaction with Lithium Methyltriolborate
    Y. Yamamoto, K. Ikizakura, H. Ito, N. Miyaura, Molecules, 2013, 18, 430-439
    DOI: 10.3390/molecules18010430


  • Me-BIPAM for the Synthesis of Optically Active 3-Aryl-3-Hydroxy-2-Oxindoles by Ruthenium-Catalyzed Addition of Arylboronic Acids to Isatins
    Y. Yamamoto, M. Yohda, T. Shirai, H. Ito, N. Miyaura, Chem. Asian J., 2012, 7, 2446-2449
    DOI: 10.1002/asia.201200481