SAWAMURA, Masaya

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SAWAMURA, Masaya
Professor
Faculty of Science, Hokkaido University
ICReDD Fellow
Research Areas
Catalysis, New catalytic reactions involving transition metals and/or small molecule
Related Website
Contact

sawamura atmark sci.hokudai.ac.jp

About the Research

Research Theme

Development of new catalytic reactions using transition metals

Keyword

Organometallic chemistry
Research Outline

My research is on the development of super-efficient and powerful catalysts and chemical reactions through ligand design. The ligand is the molecule that binds to a metal, thus dramatically changing the property of a metal. Fascinated by the very beautiful molecular structure of biological enzymes, I aim to synthesise such a catalyst by the combination of rather simple molecules, rather than preparing very complex and big molecules paying a large synthetic cost.

My work relates to two important trends and demands in my field. One is the utilization of unreactive chemical bonds, for example the unactivated C-H bond, to produce molecular complexity. The other is the asymmetric synthesis of chiral molecules from simple achiral molecules that is important for pharmaceutical science.

The Researcher’s Perspective

Since having become a professional scientist, I like to think that I have become much better at writing, at least in the Japanese language. The necessity to explain my work and its importance to other people in written but also in spoken form gave me an opportunity to grow my abilities in this respect.

 

Representative Research Achievements

  • Enantiocontrol by Assembled Attractive Interactions in Copper-catalyzed Asymmetric Direct Alkynylation of a-Ketoesters with Terminal Alkynes: OH···O/sp3-CH···O Two-point Hydrogen-bonding Combined with Dispersive Attractions
    Schwarzer, M. C.; Fujioka, A.; Ishii, T.; Ohmiya, H.; Mori, S.; Sawamura, M., Chem. Sci., 2018, 9, 3484–3493
    DOI : 10.1039/C8SC00527C
  • A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis
    Iwai, T.; Harada, T.; Shimada, H.; Asano, K.; Sawamura, M., ACS Catal., 2017, 7, 1681–1692
    DOI : 10.1021/acscatal.6b02988
  • Copper-Catalyzed Enantioselective Allylic Alkylation of Terminal Alkyne Pronucleophiles
    Harada, A.; Makida, Y.; Sato, T.; Ohmiya, H.; Sawamura, M., J. Am. Chem. Soc., 2014, 136, 13932–13939
    DOI : 10.1021/ja5084333
  • Threefold Cross-Linked Polystyrene-Triphenylphosphane Hybrids: Mono-P-Ligating Behaviors and Catalytic Applications for Aryl Chloride Cross-Coupling and C(sp3)–H Borylation
    Iwai, T.; Harada, T.; Hara, K.; Sawamura, M., Angew. Chem. Int. Ed. 2013, 52, 12322–12326
    DOI : 10.1002/anie.201306769
  • Synthesis of Primary and Secondary Alkylboronates through Site-Selective C(sp3)–H Activation with Silica-Supported Monophosphine–Ir Catalysts
    Kawamorita, S.; Murakami, R; Iwai, T.; Sawamura, M., J. Am. Chem. Soc., 2013, 135, 2947–2950
    DOI : 10.1021/ja3126239

Related Research

Publications

2025

  • Photocatalytic Cyclization of 2-Phosphinobiaryls to Trivalent Dibenzophospholes
    Y. Masuda, Y. Harabuchi, Y. Kawamura, N. Morooka, S. Maeda, M. Sawamura, Acs Catalysis, 2025, 15, 6514–6524
    DOI: 10.1021/acscatal.5c01369
  • Photoinduced Direct β-Allylation of Carboxylic Acids Enabled by Boron Catalysis with a Mixed Two-Ligand System
    K. Sun, Y. Heike, Y. Yoshida, M. Sawamura, D. Huang, Y. Shimizu, Chemcatchem, 2025, ,
    DOI: 10.1002/cctc.202500091

2024

  • Photocatalytic Alkene-Migrative Chain Elongation of 2-Phosphinostyrenes with Aldehydes
    H. Mori, A. Sakurada, M. Sawamura, Y. Masuda, Org. Lett., 2024, 27, 1, 439–443
    DOI: 10.1021/acs.orglett.4c04424
  • Oxyamination of Alkenes Enabled by Direct Photoexcitation of Fluorenone Oxime Derivatives
    A. Tagata, M. Sawamura, Y. Shimizu, Chem. Lett., 2024, 53 (12),
    DOI: 10.1093/chemle/upae216
  • Photoinduced Enantioselective Triplet Radical Reaction on Metal: Copper-Catalyzed Conjugate Addition of Acylsilanes to α,β-Unsaturated Ketones and Aldehydes
    Y. Masuda, Y. Ueda, A. Sueki, J. Shimosato, K. Nishimura, M. Gao, J. Hasegawa, M. Sawamura, Chem. Eur. J., 2024, 30(65), e202402564
    DOI: 10.1002/chem.202402564
  • Roles of Divinylbenzene Co-Cross-Linker in a Threefold Cross-Linked Polystyrene-Phosphine Hybrid Monolith: Impact of Cross-Linking Degree on Catalytic Performance
    H. Matsumoto, Y. Hoshino, T. Iwai, M. Sawamura, Y. Miura, European Journal of Organic Chemistry, 2024, , e202400974
    DOI: 10.1002/ejoc.202400974
  • Boron-Catalyzed Michael Reaction of Donor-Acceptor Carboxylic Acid Pairs Enabling Direct Synthesis of 1,5-Dicarboxylic Acids
    Y. Yoshida, M. Sawamura, Y. Shimizu, Org. Lett., 2024, 26 (26), 5425-5429
    DOI: 10.1021/acs.orglett.4c01542
  • Gold-Zinc Co-Catalyzed Alkynoate Hydrocarboxylation with N-Protected Amino Acids for Preparation of Storable Acylating Reagents and Racemization-Free Peptide Synthesis
    A. Sakurada, M. Sato, K. Higashida, M. Sawamura, Adv. Synth. Catal., 2024, ,
    DOI: 10.1002/adsc.202400286
  • Continuous-Flow Catalysis Using Phosphine-Metal Complexes on Porous Polymers: Designing Ligands, Pores, and Reactors
    H. Matsumoto, T. Iwai, M. Sawamura, Y. Miura, ChemPlusChem, 2024, ,
    DOI: 10.1002/cplu.202400039
  • Photoinduced Platinum-Catalyzed Reductive Allylation of α-Diketones with Allylic Carbonates
    J. Shimosato, M. Sawamura, Y. Masuda, Org. Lett., 2024, ,
    DOI: 10.1021/acs.orglett.4c00091

2023

  • Photocatalytic Aldehyde C-H Bond Phosphonioethylation with Vinylphosphonium Bromide
    H. Mori, M. Yoshida, M. Sawamura, Y. Masuda, Asian Journal of Organic Chemistry, 2023, ,
    DOI: 10.1002/ajoc.202300532
  • Gold-Zinc Cooperative Catalysis for Seven-exo-dig Hydrocarboxylation of Internal Alkynes
    M. Sato, V. K. Rawat, K. Higashida, M. Sawamura, Chem. Eur. J., 2023, ,
    DOI: 10.1002/chem.202301917
  • Sheltering Mono-P-Ligated Metal Complexes in Porous Polystyrene Monolith: Effect of Aryl Pendant Stabilizers on Catalytic Durability
    H. Matsumoto, Y. Hoshino, T. Iwai, M. Sawamura, Y. Miura, Chem. Eur. J., 2023, ,
    DOI: 10.1002/chem.202301847
  • Photocatalytic 1,2-Phosphorus-Migrative [3+2] Cycloaddition of Tri(t-Butyl)phosphine with Terminal Alkynes
    Y. Masuda, D. Ikeshita, K. Higashida, M. Yoshida, N. Ishida, M. Murakami, M. Sawamura, J. Am. Chem. Soc., 2023, 145, 34, 19060–19066
    DOI: 10.1021/jacs.3c06760
  • Dimetal-Binding Scaffold 2-(Pyridin-2-Yl)imidazo 1,5-b Pyridazine-7-Ylidene: Synthesis of Trinuclear Heterobimetallic Complexes Involving Gold-Metal Interactions
    A. Kitabayashi, Y. Ono, T. Taketsugu, M. Sawamura, K. Higashida, Chem. Eur. J., 2023, ,
    DOI: 10.1002/chem.202301673
  • Development of Phenol- NHC Chiral Ligands and Enantioselective Copper - Catalyzed Reactions
    M. Sawamura, J. Syn. Org. Chem. Jpn., 2023, 81(8), 774-786
    DOI: 10.5059/yukigoseikyokaishi.81.774
  • Sequence-Selective Three-Component Reactions of Alkyltrifluoroborates with Alpha,beta-Unsaturated Carbonyl Compounds and Vinylphosphonium Salts
    M. Yoshida, M. Sawamura, Y. Masuda, Organic Chemistry Frontiers, 2023, ,
    DOI: 10.1039/d3qo00631j
  • Direct a-Trifluoromethylthiolation of Carboxylic Acids Enabled by Boron Catalysis
    K. Sun, C. Y. D. Huang, M. Sawamura, Y. Shimizu, Synlett, 2023, ,
    DOI: 10.1055/a-2071-4465

2022

  • Boron Catalysis in the Transformation of Carboxylic Acids and Carboxylic Acid Derivatives
    M. Sawamura, Y. Shimizu, European Journal of Organic Chemistry, 2022, ,
    DOI: 10.1002/ejoc.202201249
  • Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides
    Z. S. You, Y. Masuda, T. Iwai, K. Higashida, M. Sawamura, J. Org. Chem., 2022, 87, 21, 14731–14737
    DOI: 10.1021/acs.joc.2c02048
  • Photoinduced Alcoholic Alpha-C-H Bond Anti-Markovnikov Addition to Vinylphosphonium Bromides Followed by Wittig Olefination: Two-Step Protocol for Alpha-C-H Allylic Alkylation of Alcohols
    M. Yoshida, M. Sawamura, Y. Masuda, Chemcatchem, 2022, 14,
    DOI: 10.1002/cctc.202200744
  • Construction of Heterobimetallic Catalytic Scaffold with a Carbene-Bipyridine Ligand: Gold-Zinc Two-Metal Catalysis for Intermolecular Addition of O-Nucleophiles to Nonactivated Alkynes
    V. K. Rawat, K. Higashida, M. Sawamura, Acs Catalysis, 2022, ,
    DOI: 10.1021/acscatal.2c01701
  • Silver-Catalyzed Asymmetric Aldol Reaction of Isocyanoacetic Acid Derivatives Enabled by Cooperative Participation of Classical and Nonclassical Hydrogen Bonds
    S. Sakai, A. Fujioka, K. Imai, K. Uchiyama, Y. Shimizu, K. Higashida, M. Sawamura, Adv. Synth. Catal., 2022, 364, 2333-2339
    DOI: 10.1002/adsc.202200327
  • Insights into the Mechanism of Enantioselective Copper-Catalyzed Ring-Opening Allylic Alkylation of Cyclopropanols
    A. Kitabayashi, S. Mizushima, K. Higashida, Y. Yasuda, Y. Shimizu, M. Sawamura, Adv. Synth. Catal., 2022, 364, 1855-1862
    DOI: 10.1002/adsc.202200157
  • Photoinduced Copper-Catalyzed Asymmetric Acylation of Allylic Phosphates with Acylsilanes
    Y. Ueda, Y. Masuda, T. Iwai, K. Imaeda, H. Takeuchi, K. Ueno, M. Gao, J. Y. Hasegawa, M. Sawamura, J. Am. Chem. Soc., 2022, 144, 2218-2224
    DOI: 10.1021/jacs.1c11526

2021

  • Visible Light-Induced Reductive Alkynylation of Aldehydes by Umpolung Approach
    I. Tanaka, M. Sawamura, Y. Shimizu, Org. Lett., 2021, 24, 520-524
    DOI: 10.1021/acs.orglett.1c03927
  • Synthesis of C,N,N-Cyclometalated Gold(III) Complexes with Anionic Amide Ligands
    R. Niizeki, K. Higashida, E. Mejri, M. Sawamura, Y. Shimizu, Synlett, 2021, 33, 288-292
    DOI: 10.1055/a-1673-9236
  • Visible-Light-Driven Alpha-Allylation of Carboxylic Acids
    K. Sun, M. Ueno, K. Imaeda, K. Ueno, M. Sawamura, Y. Shimizu, Acs Catalysis, 2021, 11, 9722-9728
    DOI: 10.1021/acscatal.1c02558
  • Construction of Medium-Sized Rings by Gold Catalysis
    R. L. Reyes, T. Iwai, M. Sawamura, Chemical Reviews, 2021, 121, 8926-8947
    DOI: 10.1021/acs.chemrev.0c00793
  • A Hollow-Shaped Caged Triarylphosphine: Synthesis, Characterization and Applications to Gold(I)-Catalyzed 1,8-Enyne Cycloisomerization
    T. Iwai, Y. Goto, Z. S. You, M. Sawamura, Chem. Lett., 2021, 50, 1236-1239
    DOI: 10.1246/cl.210176
  • Nickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant
    V. K. Rawat, K. Higashida, M. Sawamura, Synthesis-Stuttgart, 2021, ,
    DOI: 10.1055/a-1509-5954
  • Use of Imidazo 1,5-a Pyridin-3-Ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids
    V. K. Rawat, K. Higashida, M. Sawamura, Adv. Synth. Catal., 2021, 363, 1631-1637
    DOI: 10.1002/adsc.202001515
  • Phosphinylation of Non-Activated Aryl Fluorides through Nucleophilic Aromatic Substitution at the Boundary of Concerted and Stepwise Mechanisms
    Z. S. You, K. Higashida, T. Iwai, M. Sawamura, Angew. Chem., Int. Ed., 2021, 60, 5778-5782
    DOI: 10.1002/anie.202013544
  • Synthesis of 4-Hydroxy-2-Pyridinone Derivatives and Evaluation of Their Antioxidant/Anticancer Activities
    W. S. Hamama, E. A. Ghaith, M. E. Ibrahim, M. Sawamura, H. H. Zoorob, ChemistrySelect, 2021, 6, 1430-1439
    DOI: 10.1002/slct.202004682
  • Copper-Catalyzed Reactions of Alkylboranes
    H. Ohmiya, M. Sawamura, Bulletin of the Chemical Society of Japan, 2021, 94, 197-203
    DOI: 10.1246/bcsj.20200283

2020

  • The Scope of 3-Acetyl-4-Hydroxy-6-Methyl-2H-Pyran-2-One (DHA)
    E. A. Ghaith, H. H. Zoorob, M. E. Ibrahim, M. Sawamura, W. S. Hamamai, Current Organic Chemistry, 2020, 24, 1459-1490
    DOI: 10.2174/1385272824999200622114328
  • Convenient Synthesis of Binary and Fused Pyrazole Ring Systems: Accredited by Molecular Modeling and Biological Evaluation
    E. A. Ghaith, H. H. Zoorob, M. E. Ibrahim, M. Sawamura, W. S. Hamama, ChemistrySelect, 2020, 5, 14917-14923
    DOI: 10.1002/slct.202004014
  • Dumbbell-Shaped 2,2 '-Bipyridines: Controlled Metal Monochelation and Application to Ni-Catalyzed Cross-Couplings
    Y. Kim, T. Iwai, S. Fujii, K. Ueno, M. Sawamura, Chem. Eur. J., 2020, ,
    DOI: 10.1002/chem.202004053
  • Iridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and Sp(3)-C-H Noncovalent Interactions
    H. Murayama, Y. Heike, K. Higashida, Y. Shimizu, N. Yodsin, Y. Wongnongwa, S. Jungsuttiwong, S. Mori, M. Sawamura, Adv. Synth. Catal., 2020, 362, 4655-4661
    DOI: 10.1002/adsc.202000615
  • Polystyrene-Cross-Linking Triphenylphosphine on a Porous Monolith: Enhanced Catalytic Activity for Aryl Chloride Cross-Coupling in Biphasic Flow
    H. Matsumoto, Y. Hoshino, T. Iwai, M. Sawamura, Y. Miura, Industrial & Engineering Chemistry Research, 2020, 59, 15179-15187
    DOI: 10.1021/acs.iecr.0c02404
  • Polystyrene-Supported PPh(3)in Monolithic Porous Material: Effect of Cross-Linking Degree on Coordination Mode and Catalytic Activity in Pd-Catalyzed C-C Cross-Coupling of Aryl Chlorides
    H. Matsumoto, Y. Hoshino, T. Iwai, M. Sawamura, Y. Miura, Chemcatchem, 2020, 12, 4034-4037
    DOI: 10.1002/cctc.202000651
  • Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine
    D. L. Zhang, T. Iwai, M. Sawamura, Org. Lett., 2020, 22, 5240-5245
    DOI: 10.1021/acs.orglett.0c01905
  • Copper-Catalyzed Enantioselective Conjugate Reduction of Alpha,beta-Unsaturated Esters with Chiral Phenol-Carbene Ligands
    S. Mimura, S. Mizushima, Y. Shimizu, M. Sawamura, Beilstein Journal of Organic Chemistry, 2020, 16, 537-543
    DOI: 10.3762/bjoc.16.50

2019

  • A Polystyrene-Cross-Linking Tricyclohexylphosphine: Synthesis, Characterization and Applications to Pd-Catalyzed Cross-Coupling Reactions of Aryl Chlorides
    Arashima, J, Iwai, T, Sawamura, M, Chem. Asian J., 2019, 14, 411-415
    DOI: 10.1002/asia.201801651
  • Asymmetric Synthesis of α-Alkylidene-β-Lactams Through Copper Catalysis with a Prolinol-Phosphine Chiral Ligand
    K. Imai, Y. Takayama, H. Murayama, H. Ohmiya, Y. Shimizu, M. Sawamura, Org. Lett., 2019, 21, 1717-1721
    DOI: 10.1021/acs.orglett.9b00276
  • Boron-Catalyzed Alpha-Amination of Carboxylic Acids
    T. Morisawa, M. Sawamura, Y. Shimizu, Org. Lett., 2019, 21, 7466-7469
    DOI: 10.1021/acs.orglett.9b02769
  • Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines
    A. Nishizawa, T. Takahira, K. Yasui, H. Fujimoto, T. Iwai, M. Sawamura, N. Chatani, M. Tobisu, J. Am. Chem. Soc., 2019, 141, 7261-7265
    DOI: 10.1021/jacs.9b02751
  • Nickel-Copper-Catalyzed Hydroacylation of Vinylarenes with Acyl Fluorides and Hydrosilanes
    Y. Ueda, T. Iwai, M. Sawamura, Chem. Eur. J., 2019, 25, 9410-9414
    DOI: 10.1002/chem.201900822
  • Heterogeneous Nickel-Catalyzed Cross-Coupling Between Aryl Chlorides and Alkyllithiums Using a Polystyrene-Cross-Linking Bisphosphine Ligand
    Y. Yamazaki, N. Arima, T. Iwai, M. Sawamura, Adv. Synth. Catal., 2019, 361, 2250-2254
    DOI: 10.1002/adsc.201801713
  • Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor
    DL. Zhang, T. Iwai, M. Sawamura, Org. Lett., 2019, 21, 5867-5872
    DOI: 10.1021/acs.orglett.9b01989