伊藤

thumbnail image
伊藤
主任研究者, 副拠点長
北海道大学
研究分野
有機合成化学、有機元素化学、メカノケミストリー
関連ウェブサイト
連絡先

hajito atmark eng.hokudai.ac.jp

伊藤 肇 グループ
主任研究者
  • thumbnail image
    伊藤
教員
博士研究員
研究協力者
スタッフ

研究紹介

研究テーマ

小分子と多様な元素を用いた新規反応開発

キーワード

新反応開発, メカノ応答性マテリアル, メカノケミカル合成
研究概要

伊藤研究グループの主要トピックは以下の3つです。まず第一に、銅やホウ素、その他の金属の活用を鍵とした有機合成における新規反応開発、次に、「こする」「すりつぶす」などの力学的な力に応答して、興味深い光学特性を示す新規材料の開発、そして3つめは、メカノケミカル合成です。メカノケミカル合成は溶媒を使用しないため、これまでの有機合成プロセスよりも効率的で環境に優しいとされています。

計算化学は新規化学反応の開発にとって非常に重要な技術です。これまで実験化学者は、主に実験によるスクリーニングや偶然の発見に頼らざるを得ませんでしたが、コンピューターを活用した新手法、特に人口力誘起反応法(AFIR法)は、新規反応を予測を可能とするため、新反応探索の道標「地図」となるはずです。

研究者の思い

 新しく興味深い現象を見つけるたびに、私たちは新規プロジェクトを立ち上げます。学生にとっても、複数のプロジェクトに携わる経験ができることは有益です。素晴らしいグループメンバーとともに、日々様々な発見を楽しんでいます。

MANABIYAコースの研修内容はこちらです。MANABIYA全般について詳しく知りたい方は、こちらをクリックしてください

代表的な研究成果

  • 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

関連する研究記事

業績一覧

2021年

  • Charge-Transfer Crystal with Segregated Packing Structure Constructed with Hexaarylbenzene and Tetracyanoquinodimethane
    R. Ando, M. Jin, H. Ito, Crystengcomm, 2021, 23, 5564-5568
    DOI: 10.1039/d1ce00726b
  • Synthesis of Hydrosilylboronates via the Monoborylation of a Dihydrosilane Si-H Bond and Their Application for the Generation of Dialkylhydrosilyl Anions
    T. Takeuchi, R. Shishido, K. Kubota, H. Ito, Chem. Sci., 2021, ,
    DOI: 10.1039/d1sc01440d
  • Development of Selective Reactions Using Ball Milling
    K. Kubota, H. Ito, J. Syn. Org. Chem. Jpn., 2021, 79, 492-502
    DOI:
  • Introduction of a Luminophore into Generic Polymers via Mechanoradical Coupling with a Prefluorescent Reagent
    K. Kubota, N. Toyoshima, D. Miura, J. L. Jiang, S. Maeda, M. Jin, H. Ito, Angew. Chem., Int. Ed., 2021, 60, 16003-16008
    DOI: 10.1002/anie.202105381
  • Synthesis of Chiral Alpha-Amino Tertiary Boronates via the Catalytic Enantioselective Nucleophilic Borylation of Dialkyl Ketimines
    K. Kubota, D. Miura, T. Takeuchi, S. Osaki, H. Ito, Acs Catalysis, 2021, 11, 6733-6740
    DOI: 10.1021/acscatal.1c01689
  • Synthesis and Optical Properties of C,N-Swapped Boranils Derived from Potassium Acyltrifluoroborates
    S. Matsuura, J. Taguchi, T. Seki, H. Ito, Bulletin of the Chemical Society of Japan, 2021, 94, 1547-1552
    DOI: 10.1246/bcsj.20210024
  • Backbone-Modified C-2-Symmetrical Chiral Bisphosphine TMSQuinoxP*: Asymmetric Borylation of Racemic Allyl Electrophiles
    H. Iwamoto, Y. Ozawa, Y. Takenouchi, T. Imamoto, H. Ito, J. Am. Chem. Soc., 2021, 143, 6413-6422
    DOI: 10.1021/jacs.0c08899
  • (9-Isocyanoanthracene)gold(I) Complexes Exhibiting Two Modes of Crystal Jumps by Different Structure Change Mechanisms
    K. Kato, T. Seki, H. Ito, Inorg. Chem., 2021, 60, 10849-10856
    DOI: 10.1021/acs.inorgchem.1c00881
  • A Copper(I)-Catalyzed Radical-Relay Reaction Enabling the Intermolecular 1,2-Alkylborylation of Unactivated Olefins
    S. Akiyama, N. Oyama, T. Endo, K. Kubota, H. Ito, J. Am. Chem. Soc., 2021, 143, 5260-5268
    DOI: 10.1021/jacs.1c02050
  • Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides
    T. Seo, N. Toyoshima, K. Kubota, H. Ito, J. Am. Chem. Soc., 2021, 143, 6165-6175
    DOI: 10.1021/jacs.1c00906
  • Copper(I)-Catalyzed Stereoselective Silylative Dearomatization of Indoles and Pyrroles Using Silylboronates
    K. Hayama, R. Takahashi, K. Kubota, H. Ito, Chem. Lett., 2021, 50, 289-292
    DOI: 10.1246/cl.200725
  • Encapsulating N-Heterocyclic Carbene Binuclear Transition-Metal Complexes as a New Platform for Molecular Rotation in Crystalline Solid-State
    M. Jin, R. Ando, M. J. Jellen, M. A. Garcia-Garibay, H. Ito, J. Am. Chem. Soc., 2021, 143, 1144-1153
    DOI: 10.1021/jacs.0c11981

2020年

  • 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
  • Mechanochemical Cross-Coupling Reactions
    K. Kubota, H. Ito, Trends in Chemistry, 2020, 2, 1066-1081
    DOI: 10.1016/j.trechm.2020.09.006
  • Solid-State Radical C-H Trifluoromethylation Reactions Using Ball Milling and Piezoelectric Materials
    Y. D. Pang, J. W. Lee, K. Kubota, H. Ito, Angew. Chem., Int. Ed., 2020, 59, 22570-22576
    DOI: 10.1002/anie.202009844
  • A Glove-Box- and Schlenk-Line-Free Protocol for Solid-State C-N Cross-Coupling Reactions Using Mechanochemistry
    K. Kubota, R. Takahashi, M. Uesugi, H. Ito, Acs Sustainable Chemistry & Engineering, 2020, 8, 16577-16582
    DOI: 10.1021/acssuschemeng.0c05834
  • General Synthesis of Trialkyl- and Dialkylarylsilylboranes: Versatile Silicon Nucleophiles in Organic Synthesis
    R. Shishido, M. Uesugi, R. Takahashi, T. Mita, T. Ishiyama, K. Kubota, H. Ito, J. Am. Chem. Soc., 2020, 142, 14125-14133
    DOI: 10.1021/jacs.0c03011
  • Thermosalience in Macrocycle-Based Soft Crystals via Anisotropic Deformation of Disilanyl Architecture
    K. Omoto, T. Nakae, M. Nishio, Y. Yamanoi, H. Kasai, E. Nishibori, T. Mashimo, T. Seki, H. Ito, K. Nakamura, N. Kobayashi, N. Nakayama, H. Goto, H. Nishihara, J. Am. Chem. Soc., 2020, 142, 12651-12657
    DOI: 10.1021/jacs.0c03643
  • Photoluminescent Ferroelastic Molecular Crystals
    T. Seki, C. Feng, K. Kashiyama, S. Sakamoto, Y. Takasaki, T. Sasaki, S. Takamizawa, H. Ito, Angew. Chem., Int. Ed., 2020, 59, 8839-8843
    DOI: 10.1002/anie.201914610
  • Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by in Situ Crystallization
    T. Seo, K. Kubota, H. Ito, J. Am. Chem. Soc., 2020, 142, 9884-9889
    DOI: 10.1021/jacs.0c01739
  • Copper(I)-Catalyzed Boryl Substitution of 1-Trifluoromethyl Allenes for the Synthesis of 3-Boryl-Substituted 1,1-Gem-Difluorodienes
    S. Akiyama, S. Nomura, K. Kubota, H. Ito, J. Org. Chem., 2020, 85, 4172-4181
    DOI: 10.1021/acs.joc.9b03353
  • Silyl-Group-Directed Linear-Selective Allylation of Carbonyl Compounds with Trisubstituted Allylboronates Using a Copper(I) Catalyst
    H. Iwamoto, Y. Hayashi, Y. Ozawa, H. Ito, Acs Catalysis, 2020, 10, 2471-2476
    DOI: 10.1021/acscatal.9b05408
  • Crystal Jumping of Simple Hydrocarbons: Cooling-Induced Salient Effect of Bis-, Tri-, and Tetraphenylethene through Anisotropic Lattice Dimension Changes Without Thermal Phase Transitions
    T. Seki, T. Mashimo, H. Ito, Chem. Lett., 2020, 49, 174-177
    DOI: 10.1246/cl.190768
  • Mixed Crystal Formation of Two Gold Isocyanide Complexes with Various Ratios for Continuous Tuning of Photophysical Properties
    T. Seki, N. Toyoshima, H. Ito, Dalton Trans., 2020, 49, 2073-2076
    DOI: 10.1039/d0dt00195c
  • Stacked Nanocarbon Photosensitizer for Efficient Blue Light Excited Eu(III) Emission
    Y. Kitagawa, F. Suzue, T. Nakanishi, K. Fushimi, T. Seki, H. Ito, Y. Hasegawa, Communications Chemistry, 2020, 3, 7
    DOI: 10.1038/s42004-019-0251-z

2019年

  • Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives
    Akiyama, S, Kubota, K, Mikus, MS, Paioti, PHS, Romiti, F, Liu, QH, Zhou, YB, Hoveyda, AH, 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

2017年

  • 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

2014年

  • 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

2013年

  • 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

2012年

  • 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