澤村 正也

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澤村 正也
教授
北海道大学理学研究院
ICReDDフェロー
研究分野
触媒化学, 遷移金属/新触媒反応開発・小分子
関連ウェブサイト
連絡先

sawamura atmark sci.hokudai.ac.jp

研究紹介

研究テーマ

遷移金属を用いた新規触媒反応開発

キーワード

有機金属化学
研究概要

私は、配位子設計による超高効率で有用な触媒開発と新規化学反応開発を行っています。 配位子とは金属に結合する分子で、金属の特性を劇的に変化させるものです。 生体酵素における分子構造の美しさに魅了されて以来、複雑で大きな分子を大量の合成コストをかけて準備するよりも、単純な分子の組み合わせでそのような触媒を合成することを目指しています。

私の研究に関連する分野には重要な潮流と達成すべきことがあります。 1つは、分子の複雑さを生み出すための反応性の低い化学結合、たとえば非活性C-H結合の利用です。 もう1つは、製薬にとって重要な単純なアキラル分子からのキラル分子の不斉合成です。

 

代表的な研究成果

  • 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

関連する研究記事

業績一覧

2024年

  • 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年

  • Development of Phenol- NHC Chiral Ligands and Enantioselective Copper - Catalyzed Reactions
    M. Sawamura, J. Syn. Org. Chem. Jpn., 2023, 81(8), 774-786
    DOI:
  • 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
  • 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年

  • 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年

  • 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年

  • 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年

  • 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