Hokkaido University

Institute for Chemical Reaction Design and Discovery

2025

• Mechanochemical Activation of Metallic Lithium for the Generation and Application of Organolithium Compounds in Air
  K. Kondo, K. Kubota, H. Ito, NATURE SYNTHESIS, 2025, ,
  DOI: 10.1038/s44160-025-00753-3
  
• Solid-State Aromatic Nucleophilic Fluorination: A Rapid, Practical, and Environmentally Friendly Route to N-Heteroaryl Fluorides
  K. Kubota, T. Makino, K. Kondo, T. Seo, M. Jin, H. Ito, GREEN CHEMISTRY, 2025, ,
  DOI: 10.1039/d4gc06362g
  

2024

• Mechanochemical Generation of Aryl Barium Nucleophiles from Unactivated Barium Metal
  K. Kubota, S. Kawamura, J. Jiang, S. Maeda, H. Ito, Chem. Sci., 2024, Issue 42,
  DOI: 10.1039/d4sc05361c
  
• Dissolution-Limited Reactions in Solid-State Synthesis
  T. Yamamoto, K. Kubota, H. Ito, NIHON REOROJI GAKKAISHI, 2024, 52(2), 161-170
  DOI: 10.1678/rheology.52.161
  
• Solid-State Nickel(0)-Mediated Yamamoto Coupling Enabled by Mechanochemistry
  K. Kubota, N. Shizukuishi, S. Kubo, H. Ito, Chem. Lett., 2024, 53,
  DOI: 10.1093/chemle/upae056
  
• Highly Efficient and Air-Tolerant Calcium-Based Birch Reduction Using Mechanochemistry
  K. Kubota, Y. Fukuzawa, K. Kondo, Y. P. Gao, H. Ito, Chem. Lett., 2024, 53, 4,
  DOI: 10.1093/chemle/upae060
  
• 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

• 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

• 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

• 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

• 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

• 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

• 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

• 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

• 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