久保田 浩司

thumbnail image
久保田 浩司
准教授
北海道大学大学院工学研究院
関連ウェブサイト
伊藤 肇 グループ
主任研究者
教員
博士研究員
研究協力者
  • thumbnail image
    久保田 浩司
スタッフ
  • 婷钰(フティンユー)

研究紹介

研究テーマ

Development of New Reactions Using Mechanochemistry

キーワード

Mechanochemistry, Ball Mill, Catalysis, Synthetic Method
経歴

経歴書を参照願います。

代表的な研究成果

  • Redox reactions of small organic molecules using ball milling and piezoelectric materials
    Kubota, K.*; Pang, Y.; Miura, A.; Ito, H.,* Science, 2019, 366, 1500
    DOI: 10.1126/science.aay8224
  • 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)
    Kubota, K.*; Takahashi, R.; Ito, H.,* Chem. Sci., 2019, 10, 5837
    DOI: 10.1039/C9SC01711A
  • Olefin-accelerated solid-state C-N cross-coupling reactions using mechanochemistry
    Kubota, K.*; Seo, T.; Koide, K.; Hasegawa, Y.; Ito, H.,* Nature Commun., 2019, 10, 111 
    DOI: 10.1038/s41467-018-08017-9
  • Solid-State Suzuki-Miyaura Cross-Coupling Reactions: Olefin-Accelerated C–C Coupling Using Mechanochemistry
    Seo, T.; Ishiyama, T.; Kubota, K.*; Ito, H.,* Chem. Sci., 2019, 10, 8202 
    DOI: 10.1039/C9SC02185J
  • Palladium Oxidative Addition Complexes for Peptide and Protein Cross-linking
    Kubota, K.; Dai, P.; Pentelute B. L.*; Buchwald S. L.,* J. Am. Chem. Soc., 2018, 140, 3128 
    DOI: 10.1021/jacs.8b00172

関連する研究記事

業績一覧

2024年

  • Mechanochemistry Enabling Highly Efficient Birch Reduction Using Sodium Lumps and D-(+)-Glucose
    K. Kondo, K. Kubota, H. Ito, Chem. Sci., 2024, ,
    DOI: 10.1039/d3sc06052g
  • Solid-State Mechanochemistry for the Rapid and Efficient Synthesis of Tris-Cyclometalated Iridium(iii) Complexes
    K. Kubota, T. Endo, H. Ito, Chem. Sci., 2024, ,
    DOI: 10.1039/d3sc05796h
  • Ring Expansion of Cyclic Boronates via Oxyboration of Arynes
    Y. Shiratori, J. L. Jiang, K. Kubota, S. Maeda, H. Ito, J. Am. Chem. Soc., 2024, 146, 3, 1765-1770
    DOI: 10.1021/jacs.3c11851

2023年

  • Using Mechanochemistry to Activate Commodity Plastics as Initiators for Radical Chain Reactions of Small Organic Molecules
    K. Kubota, J. L. Jiang, Y. Kamakura, R. Hisazumi, T. Endo, D. Miura, S. Kubo, S. Maeda, H. Ito, J. Am. Chem. Soc., 2023, 146, 1062-1070
    DOI: 10.1021/jacs.3c12049
  • Mechanochemical Synthesis of Non-Solvated Dialkylalumanyl Anion and XPS Characterization of Al(I) and Al(II) Species
    S. Kurumada, R. Yamanashi, K. Sugita, K. Kubota, H. Ito, S. Ikemoto, C. Q. Chen, T. Moriyama, S. Muratsugu, M. Tada, T. Koitaya, T. Ozaki, M. Yamashita, Chem. Eur. J., 2023, ,
    DOI: 10.1002/chem.202303073
  • Exploring Novel Synthetic Concepts and Strategies Using Mechanochemistry
    Kubota, K., Bulletin of the Chemical Society of Japan, 2023, 96, 913-930
    DOI: 10.1246/bcsj.20230157
  • Stereospecific Synthesis of Silicon-Stereogenic Optically Active Silylboranes and General Synthesis of Chiral Silyl Anions
    X. H. Wang, C. Feng, J. L. Jiang, S. Maeda, K. Kubota, H. Ito, Nat. Commun., 2023, 14, 5561
    DOI: 10.1038/s41467-023-41113-z
  • Solid-State Mechanochemical Cross-Coupling of Insoluble Substrates into Insoluble Products by Removable Solubilizing Silyl Groups: Uniform Synthesis of Nonsubstituted Linear Oligothiophenes
    K. Kubota, K. Kondo, T. Seo, M. G. Jin, H. Ito, RSC Advances, 2023, 13, 28652-28657
    DOI: 10.1039/d3ra05571j
  • Dual Nickel(II)/Mechanoredox Catalysis: Mechanical-Force-Driven Aryl-Amination Reactions Using Ball Milling and Piezoelectric Materials
    T. Seo, K. Kubota, H. Ito, Angew. Chem., Int. Ed., 2023, ,
    DOI: 10.1002/anie.202311531
  • Solid-State Silver-Catalyzed Ring-Opening Fluorination of Cyclobutanols by Using Mechanochemistry
    R. Isshiki, K. Kubota, H. Ito, Synlett, 2023, ,
    DOI: 10.1055/a-2021-9599
  • Mechanochemical Approach for Air-Tolerant and Extremely Fast Lithium-Based Birch Reductions in Minutes
    Y. P. Gao, K. Kubota, H. Ito, Angew. Chem., Int. Ed., 2023, ,
    DOI: 10.1002/anie.202217723
  • In Situ and Real-Time Visualization of Mechanochemical Damage in Double-Network Hydrogels by Prefluorescent Probe via Oxygen- Relayed Radical Trapping
    Y. Zheng, J. L. Jiang, M. Jin, D. Miura, F. X. Lu, K. Kubota, T. Nakajima, S. Maeda, H. Ito, J. P. Gong, J. Am. Chem. Soc., 2023, 145, 7376-7389
    DOI: 10.1021/jacs.2c13764
  • Mechanochemistry-Directed Ligand Design: Development of a High-Performance Phosphine Ligand for Palladium-Catalyzed Mechanochemical Organoboron Cross-Coupling
    T. Seo, K. Kubota, H. Ito, J. Am. Chem. Soc., 2023, 145, 6823-6837
    DOI: 10.1021/jacs.2c13543

2022年

  • Mechanochemical Protocol Facilitates the Generation of Arylmanganese Nucleophiles from Unactivated Manganese Metal
    R. Takahashi, P. Gao, K. Kubota, H. Ito, Chem. Sci., 2022, ,
    DOI: 10.1039/d2sc05468j
  • Cu(I)-Catalyzed Enantioselective Gamma-Boryl Substitution of Trifluoromethyl- and Silyl-Substituted Alkenes
    N. Oyama, S. Akiyama, K. Kubota, T. Imamoto, H. Ito, European Journal of Organic Chemistry, 2022, 2022,
    DOI: 10.1002/ejoc.202200664
  • Solid-State Cross-Coupling Reactions of Insoluble Aryl Halides under Polymer-Assisted Grinding Conditions
    K. Kubota, T. Seo, H. Ito, Faraday Discussions, 2022, ,
    DOI: 10.1039/d2fd00121g
  • Mechanochemically Generated Calcium-Based Heavy Grignard Reagents and Their Application to Carbon-Carbon Bond-Forming Reactions
    P. Gao, J. L. Jiang, S. Maeda, K. Kubota, H. Ito, Angew. Chem., Int. Ed., 2022, ,
    DOI: 10.1002/anie.202207118
  • Palladium-Catalyzed Solid-State Borylation of Aryl Halides Using Mechanochemistry
    K. Kubota, E. Baba, T. Seo, T. Ishiyama, H. Ito, Beilstein Journal of Organic Chemistry, 2022, 18, 855-862
    DOI: 10.3762/bjoc.18.86
  • Insight into the Reactivity Profile of Solid-State Aryl Bromides in Suzuki-Miyaura Cross-Coupling Reactions Using Ball Milling
    K. Kubota, K. Kondo, T. Seo, H. Ito, Synlett, 2022, 33, 898-902
    DOI: 10.1055/a-1748-3797

2021年

  • Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry
    R. Takahashi, T. Seo, K. Kubota, H. Ito, Acs Catalysis, 2021, 11, 14803-14810
    DOI: 10.1021/acscatal.1c03731
  • Efficient Access to Materials-Oriented Aromatic Alkynes via the Mechanochemical Sonogashira Coupling of Solid Aryl Halides with Large Polycyclic Conjugated Systems
    Y. P. Gao, C. Feng, T. Seo, K. Kubota, H. Ito, Chem. Sci., 2021, 13, 430-438
    DOI: 10.1039/d1sc05257h
  • Solid-State C-N Cross-Coupling Reactions with Carbazoles as Nitrogen Nucleophiles Using Mechanochemistry
    K. Kubota, T. Endo, M. Uesugi, Y. Hayashi, H. Ito, ChemSusChem, 2021, 15,
    DOI: 10.1002/cssc.202102132
  • Mechanochemical Synthesis of Magnesium-Based Carbon Nucleophiles in Air and Their Use in Organic Synthesis
    R. Takahashi, A. Q. Hu, P. Gao, Y. P. Gao, Y. D. Pang, T. Seo, J. L. Jiang, S. Maeda, H. Takaya, K. Kubota, H. Ito, Nat. Commun., 2021, 12,
    DOI: 10.1038/s41467-021-26962-w
  • 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, 12, 11799-11804
    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
  • 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

2020年

  • Controlling the Gate-Sorption Properties of Solid Solutions of Werner Complexes by Varying Component Ratios
    S. Noro, Y. Song, Y. Tanimoto, Y. Hijikata, K. Kubo, T. Nakamura, Dalton Trans., 2020, 49, 9438-9443
    DOI: 10.1039/d0dt01355b
  • 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
  • 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
  • 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

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
  • 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
  • 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
  • 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

2017年

  • Structural Diversification of Light-Metal Coordination Polymers Using 4-(Methylsulfonyl)benzoate with a Charge-Polarized Neutral Methylsulfonyl Coordination Moiety
    R. Ochi, S-i. Noro, Y. Hijikata, K. Kubo, T. Nakamura, Eur. J. Inorg. Chem., 2017, 2017, 4013-4019
    DOI: 10.1002/ejic.201700627

2015年

  • High CO2/CH4 Selectivity of a Flexible Copper(II) Porous Coordination Polymer under Humid Conditions
    S-i. Noro, R. Matsuda, Y. Hijikata, Y. Inubushi, S. Takeda, S. Kitagawa, Y. Takahashi, M. Yoshitake, K. Kubo, T. Nakamura, ChemPlusChem, 2015, 80, 1517-1524
    DOI: 10.1002/cplu.201500278
  • Porous Coordination Polymers with Ubiquitous and Biocompatible Metals and a Neutral Bridging Ligand
    S-i. Noro, J. Mizutani, Y. Hijikata, R. Matsuda, H. Sato, S. Kitagawa, K. Sugimoto, Y. Inubushi, K. Kubo, T. Nakamura, Nat. Commun., 2015, 6, 5851
    DOI: 10.1038/ncomms6851

2013年

  • Rational Synthesis of a Porous Copper(II) Coordination Polymer Bridged by Weak Lewis-Base Inorganic Monoanions Using an Anion-Mixing Method
    S-i. Noro, K. Fukuhara, Y. Hijikata, K. Kubo, T. Nakamura, Inorg. Chem., 2013, 52, 5630-5632
    DOI: 10.1021/ic400276c
  • Anion-Dependent Host-Guest Properties of Porous Assemblies of Coordination Complexes (PACs), [Cu(A)2(py)4] (A = PF6, BF4, CF3SO3, and CH3SO3; py = Pyridine), Based on Werner-Type Copper(II) Complexes in the Solid State
    S-i. Noro, K. Fukuhara, K. Sugimoto, Y. Hijikata, K. Kubo, T. Nakamura, Dalton Trans., 2013, 42, 11100-11110
    DOI: 10.1039/c3dt51104a