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Development of Highly Active Transition Metal Catalysts Based on Solid Support Strategies

Planned Research

Project AreaPrecise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions
Project/Area Number 15H05801
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionHokkaido University

Principal Investigator

Sawamura Masaya  北海道大学, 理学研究院, 教授 (40202105)

Project Period (FY) 2015-06-29 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥43,160,000 (Direct Cost: ¥33,200,000、Indirect Cost: ¥9,960,000)
Fiscal Year 2019: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000)
Fiscal Year 2018: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000)
Fiscal Year 2017: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000)
Fiscal Year 2016: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000)
Fiscal Year 2015: ¥6,240,000 (Direct Cost: ¥4,800,000、Indirect Cost: ¥1,440,000)
Keywords触媒設計 / ホスフィン / ポリスチレン / 固相担持 / 架橋剤 / ニッケル / アミノ化 / クロスカップリング / 有機リチウム / ナノ材料 / 触媒・化学プロセス / 銅 / コバルト / ヒドロホウ素化 / CO2固定化 / C-H活性化 / C-H官能基化 / 合成化学 / 有機化学
Outline of Final Research Achievements

Polystyrene(PS)-supported phosphines are widely used for heterogeneous metal catalysis. The phosphine moieties have generally significant mobility even in cross-linked PS resins, and hence exhibit ligand properties similar to those of their homogeneous counterparts. In many cases, however, the polymer chain causes unfavorable steric effects, resulting in reduced catalyst efficiency. We prepared a new type of PS-phosphine hybrid (PS-DPPBz) through radical emulsion copolymerization of styrene monomers in the presence of tetravinylated 1,2-bis(diphenylphosphino)benzene. PS-DPPBz exhibited good swelling properties with aprotic organic solvents.
As a conceptual advance of our studies with solid-immobilized ligand toward enantioselective reactions, we showed that the BINOL-based monodentate phosphite chiral ligand enabled the highly enantioselective Ir-catalyzed directed borylation of unactivated methylene C(sp3)-H bonds in saturated hydrocarbon frameworks of substituted heteroarenes.

Academic Significance and Societal Importance of the Research Achievements

分離・再利用が容易な高分子固定化金属触媒による合成プロセスの効率化が期待される。しかし、高分子鎖の立体障害によって触媒活性がしばしば低下する。我々は、複数の重合部位を有するホスフィンを高分子架橋剤とすることで金属配位点を空間的に孤立化させて高活性金属種を生成する手法を開発した。単座ホスフィンを3点架橋剤として得られるPS-TPPや2座ホスフィンを4点架橋剤とするPS-DPPBzが代表例である。

Report

(6 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (111 results)

All 2020 2019 2018 2017 2016 2015 Other

All Journal Article (25 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 25 results,  Open Access: 3 results,  Acknowledgement Compliant: 3 results) Presentation (82 results) (of which Int'l Joint Research: 29 results,  Invited: 51 results) Remarks (3 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Asymmetric Synthesis of a-Aminoboronates via Rhodium-Catalyzed Enantioselective C(sp3)-H Borylation2020

    • Author(s)
      Reyes, R. L., Sato, M., Iwai, T., and Sawamura, M.
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 1 Pages: 589-597

    • DOI

      10.1021/jacs.9b12013

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Copper-Catalyzed Enantioselective Conjugate Reduction of α,β-Unsaturated Esters with Phenol-Carbene Chiral Ligand2020

    • Author(s)
      Mimura Shohei、Mizushima Sho、Shimizu Yohei、Sawamura Masaya
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 16 Pages: 537-543

    • DOI

      10.3762/bjoc.16.50

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Polystyrene‐Supported PPh3 in Macroporous Monolith: Effect of Cross‐Linking Degree on Coordination Mode and Catalytic Activity in Pd‐Catalyzed C‐C Cross‐Coupling of Aryl Chlorides2020

    • Author(s)
      Matsumoto Hikaru、Hoshino Yu、Iwai Tomohiro、Sawamura Masaya、miura yoshiko
    • Journal Title

      ChemCatChem

      Volume: 12 Issue: 16 Pages: 4034-4037

    • DOI

      10.1002/cctc.202000651

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Asymmetric Synthesis of α-Alkylidene-β-Lactams through Copper Catalysis with a Prolinol-Phosphine Chiral Ligand2019

    • Author(s)
      Imai Koji、Takayama Yurie、Murayama Hiroaki、Ohmiya Hirohisa、Shimizu Yohei、Sawamura Masaya
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 6 Pages: 1717-1721

    • DOI

      10.1021/acs.orglett.9b00276

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel‐Copper‐Catalyzed Hydroacylation of Vinylarenes with Acyl Fluorides and Hydrosilanes2019

    • Author(s)
      Ueda Yusuke、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 40 Pages: 9410-9414

    • DOI

      10.1002/chem.201900822

    • NAID

      120006844535

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed Asymmetric Borylation of Unactivated Methylene C(sp3)-H Bonds2019

    • Author(s)
      Reyes Ronald L.、Iwai Tomohiro、Maeda Satoshi、Sawamura Masaya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 17 Pages: 6817-6821

    • DOI

      10.1021/jacs.9b01952

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines2019

    • Author(s)
      Nishizawa Akihiro、Takahira Tsuyoshi、Yasui Kosuke、Fujimoto Hayato、Iwai Tomohiro、Sawamura Masaya、Chatani Naoto、Tobisu Mamoru
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 18 Pages: 7261-7265

    • DOI

      10.1021/jacs.9b02751

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor2019

    • Author(s)
      Zhang Deliang、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 15 Pages: 5867-5872

    • DOI

      10.1021/acs.orglett.9b01989

    • NAID

      120006869882

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Boron-Catalyzed α-Amination of Carboxylic Acids2019

    • Author(s)
      Morisawa Takuto、Sawamura Masaya、Shimizu Yohei
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 18 Pages: 7466-7469

    • DOI

      10.1021/acs.orglett.9b02769

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Polystyrene‐Cross‐Linking Tricyclohexylphosphine: Synthesis, Characterization and Applications to Pd‐Catalyzed Cross‐Coupling Reactions of Aryl Chlorides2019

    • Author(s)
      Arashima Junya、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 14 Issue: 3 Pages: 411-415

    • DOI

      10.1002/asia.201801651

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Heterogeneous Nickel‐Catalyzed Cross‐Coupling between Aryl Chlorides and Alkyllithiums Using a Polystyrene‐Cross‐Linking Bisphosphine Ligand2019

    • Author(s)
      Yamazaki Yuki、Arima Nozomi、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 361 Issue: 10 Pages: 2250-2254

    • DOI

      10.1002/adsc.201801713

    • NAID

      120006798317

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Properties, and Catalytic Application of a Triptycene-Type Borate-Phosphine Ligand2018

    • Author(s)
      Konishi Shota、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Organometallics

      Volume: 37 Issue: 12 Pages: 1876-1883

    • DOI

      10.1021/acs.organomet.8b00113

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] P,P,P′,P′-Tetraethynylated Bisphosphine and P-C-P Pincer Ligands with Bulky End Caps: Synthesis, Coordination Properties and Application to Platinum-catalyzed 1,8-Enyne Cycloisomerization2018

    • Author(s)
      Iwai Tomohiro、Shibaike Kazutaka、Sawamura Masaya
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 9 Pages: 1162-1164

    • DOI

      10.1246/cl.180501

    • NAID

      130007472106

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed amination of aryl fluorides with primary amines2018

    • Author(s)
      Harada Tomoya、Ueda Yusuke、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 14 Pages: 1718-1721

    • DOI

      10.1039/c7cc08181b

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantiocontrol by assembled attractive interactions in copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes: OH-O/sp3-CH-O two-point hydrogen bonding combined with dispersive attractions2018

    • Author(s)
      Schwarzer Martin C.、Fujioka Akane、Ishii Takaoki、Ohmiya Hirohisa、Mori Seiji、Sawamura Masaya
    • Journal Title

      Chemical Science

      Volume: 9 Issue: 14 Pages: 3484-3493

    • DOI

      10.1039/c8sc00527c

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Exploring the full catalytic cycle of rhodium(I)-BINAP-catalysed isomerisation of allylic amines: a graph theory approach for path optimisation2017

    • Author(s)
      Yoshimura Takayoshi、Maeda Satoshi、Taketsugu Tetsuya、Sawamura Masaya、Morokuma Keiji、Mori Seiji
    • Journal Title

      Chemical Science

      Volume: 8 Issue: 6 Pages: 4475-4488

    • DOI

      10.1039/c7sc00401j

    • NAID

      120006324922

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Polystyrene-Cross-Linking Ortho-Substituted Triphenylphosphines: Synthesis, Coordination Properties, and Application to Pd-Catalyzed Cross-Coupling of Aryl Chlorides2017

    • Author(s)
      Tomohiro Iwai, Kiichi Asano, Tomoya Harada, Masaya Sawamura
    • Journal Title

      Bulletine of Chemical Society of Japan

      Volume: 90 Issue: 8 Pages: 943-949

    • DOI

      10.1246/bcsj.20170141

    • NAID

      130005973622

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Rh- or Ir-catalyzed Directed C(sp<sup>3</sup>)–H Borylation with Phosphoramidite Chiral Ligands2017

    • Author(s)
      Reyes Ronald L.、Harada Tomoya、Taniguchi Tohru、Monde Kenji、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 12 Pages: 1747-1750

    • DOI

      10.1246/cl.170853

    • NAID

      130006243163

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Cyclobutene-Fused Eight-Membered Carbocycles through Gold-Catalyzed Intramolecular Enyne [2+2] Cycloaddition2017

    • Author(s)
      Iwai Tomohiro、Ueno Masahiro、Okochi Hiori、Sawamura Masaya
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 360 Issue: 4 Pages: 670-675

    • DOI

      10.1002/adsc.201701193

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a-Quaternary Formimides and Aldehydes through Umpolung Asymmetric Copper Catalysis with Isocyanides2017

    • Author(s)
      Kentaro Hojoh, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Journal of the American Chemical Society

      Volume: 139 Issue: 6 Pages: 2184-2187

    • DOI

      10.1021/jacs.6b12881

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis2017

    • Author(s)
      Tomohiro Iwai, Tomoya Harada, Hajime Shimada, Kiichi Asano, Masaya Sawamura
    • Journal Title

      ACS Catalysis

      Volume: 7 Issue: 3 Pages: 1681-1692

    • DOI

      10.1021/acscatal.6b02988

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Coordination Properties, and Catalytic Application of Triarylmethane-Monophosphines2016

    • Author(s)
      Tomohiro Iwai, Ryotaro Tanaka, Masaya Sawamura
    • Journal Title

      Organometallics

      Volume: 35 Issue: 23 Pages: 3959-3969

    • DOI

      10.1021/acs.organomet.6b00752

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Enantioselective Allyl-Allyl Coupling between Allylic Boronates and Phosphates with a Phenol/N-Heterocyclic Carbene Chiral Ligand2016

    • Author(s)
      Yuto Yasuda, Hirohisa Ohmiya, Masaya Sawamura
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 36 Pages: 10816-10820

    • DOI

      10.1002/anie.201605125

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Site-selective and Stereoselective C(sp3)-H Borylation of Alkyl Side Chains of 1,3-Azoles with a Silica-Supported Monophosphine-Ir Catalyst.2016

    • Author(s)
      Ryou Murakami, Tomohiro Iwai, Masaya Sawamura.
    • Journal Title

      Synlett.

      Volume: 27 Issue: 08 Pages: 1187-1192

    • DOI

      10.1055/s-0035-1561599

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Silica-supported Triptycene-type Phosphine. Synthesis, Characterization, and Application to Pd-Catalyzed Suzuki-Miyaura Cross-coupling of Chloroarenes.2015

    • Author(s)
      Tomohiro Iwai, Shouta Konishi, Tatuya Miyazaki, Souichirou Kawamorita, Natumi Yokokawa, Hirohisa Ohmiya, Masaya Sawamura.
    • Journal Title

      ACS Catal.

      Volume: 5 Issue: 12 Pages: 7254-7264

    • DOI

      10.1021/acscatal.5b00904

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Presentation] Ligand-Enabled Selective Borylation of C(sp2)-H and C(sp3)-H Bonds2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      The 27th French-Japanese Symposium on Medicinal and Fine Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Enantioselective Methylene C(sp3)-H Borylation2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      The 47th Naito Conference on "C-H Activation and Transformation"
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Asymmetric Synthesis of α-Aminoalkylboronates through Rh-Catalyzed Enantioselective C(sp3)-H Borylation2019

    • Author(s)
      Masaya Sawamura, Ronald Reyes, Tomohiro Iwai, Satoshi Maeda
    • Organizer
      20th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS20)
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Catalytic Enantioselective C(sp3)-H Borylation2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      7th Latin American Symposium on Coordination and Organometallic Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Noncovalent Interactions in Ir-Catalyzed Enantioselective C(sp3-H Borylation2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      1st International Conferences on Noncovalent Interactions (ICNI-2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalytic Enantioselective C(sp3)-H Borylation: Mechanism and Applications2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      The 9th Junior International Conference on Cutting-Edge Organic Chemistry in Asia (Junior ICCEOCA-9)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Ligand-Enabled Selective Borylation of C(sp2)-H and C(sp3)-H Bonds2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      NOST Organic Chemistry & Biomolecular Chemistry Conference
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalytic Enantioselective C(sp3)-H Borylation2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      The 2nd ICReDD International Symposium
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Asymmetric Synthesis of α-Aminoboronates via Rhodium-Catalyzed Enantioselective C(sp3)-H Borylation2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      The 2nd Japan Germany Singapore Trilateral Symposium on Precision Synthesis and Catalysis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Experimantal and Computational Approach to Innovatve Asymmetric C-H Functionalization2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      MANA Seminar
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Enantioselective Borylation of Unactivated C(sp3)-H Bonds2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      The Hokkaido University & Peking University Joint Symposium
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Non-covalent Interactions in Our Studies on Asymmetric Transition Metal Catalysis2019

    • Author(s)
      Masaya Sawamura
    • Organizer
      3rd Workshop of SPP 1807: Central of London dispersion interactions in molecular chemistry
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 固定化ホスフィンと遷移金属による触媒デザイン2018

    • Author(s)
      澤村正也
    • Organizer
      第7回JACI/GSCシンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Catalytic Asymmetric Borylation of Unactivated Methylene C-H Bonds2018

    • Author(s)
      Ronald L. Reyes, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      The 28th International Conference on Organometallic Chemistry
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Iridium-Catalyzed Asymmetric Borylation of Methylene C-H Bonds2018

    • Author(s)
      onald L. Reyes, Tomohiro Iwai, Satoshi Maeda, Masaya Sawamura
    • Organizer
      The 4th International Symposium on C-H Activation (ISCHA4)
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 高分子ゲルによる触媒デザイン2018

    • Author(s)
      澤村正也
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Iridium-Catalyzed Asymmetric Borylation of Unactivated Methylene C-H Bonds2018

    • Author(s)
      Ronald L. Reyes, Tomohiro Iwai, Satoshi Maeda, Masaya Sawamura
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] C-H不斉変換触媒の開発2018

    • Author(s)
      澤村正也
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] ポリスチレン架橋ビスホスフィン配位子を用いたニッケル触媒村橋カップリング反応2018

    • Author(s)
      岩井智弘・山﨑勇輝・有馬望・澤村正也
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 触媒のチカラを引き出す配位子設計と反応開発2018

    • Author(s)
      澤村正也
    • Organizer
      第8回CSJ化学フェスタ2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Catalytic Enantioselective Borylation of Unactivated Methylene C-H Bonds2018

    • Author(s)
      Masaya Sawamura
    • Organizer
      The Junior International Conference on Cutting-Edge Organic Chemistry in Asia
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Catalytic Enantioselective Borylation of Unactivated Methylene C-H Bonds2018

    • Author(s)
      Ronald L. Reyes, Tomohiro Iwai, Satoshi Maeda, Masaya Sawamura
    • Organizer
      The 13th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-13)
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 不斉触媒反応と非共有結合相互作用2018

    • Author(s)
      澤村正也
    • Organizer
      大塚創薬化学シンポジウム2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Catalytic Asymmetric Borylation of Unactivated Methylene C-H Bonds2018

    • Author(s)
      Masaya Sawamura
    • Organizer
      第6回日英触媒的不斉合成シンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Iridium-Catalyzed Enantioselective Borylation of Methylene C-H Bonds Enablebled by Chiral Monophosphite Ligands2018

    • Author(s)
      Masaya Sawamura
    • Organizer
      International Conference on Phosphorus, Boron and Silicon (PBSi 2018)
    • Related Report
      2018 Annual Research Report
  • [Presentation] 配位子設計のおもしろさ2018

    • Author(s)
      澤村正也
    • Organizer
      日本薬学会東海支部特別講演会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Transition Metal Catalysis of Polystyrene-Cross-Linking Bisphosphines2018

    • Author(s)
      Masaya Sawamura
    • Organizer
      International Conference on Chemistry for Human Development (ICCHD-2018)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Ligand Design for Efficient Organic Synthesis2018

    • Author(s)
      Masaya Sawamura
    • Organizer
      Lecture at IIT Madras
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Ni-catalyzed Murahashi Coupling in Polystyrene Gel2018

    • Author(s)
      Nozomi Arima, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      IRCCS-JST CREST Joint Symposium “Chemical Sciences facing difficult challenges"
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] High-performance Transition Metal Catalysts with Polystyrene-cross-linking Phosphine Ligands2018

    • Author(s)
      Masaya Sawamura
    • Organizer
      Pure and Applied Chemistry International Conference 2018
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] New Concepts from Ligand Design2018

    • Author(s)
      Masaya Sawamura
    • Organizer
      Chulabhorn Research Institute Seminar
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 芳香族カルバメートの脱炭酸アミノ化反応の開発とその機構研究2018

    • Author(s)
      鳶巣守, 西澤彰宏, 岩井智弘, 澤村正也, 茶谷直人
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Rhodium- or Iridium-Catalyzed Enantioselective C(sp3)-H Borylation with Chiral Monophosphine Ligands2018

    • Author(s)
      Ronald Reyes, Tomoya Harada, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ポリスチレン架橋トリアルキルホスフィンの合成とパラジウム触媒クロスカップリングへの応用2018

    • Author(s)
      荒島純弥, 岩井智弘, 澤村正也
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] キラルプロリノール-ホスフィン-銅触媒を用いた末端アルキンによるα-ケトエステルの不斉直接アルキニル化2018

    • Author(s)
      藤岡茜, Martin Schwarzer C, 石井孝興, 大宮寛久, 森聖治, 澤村正也
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of Asymmetric Copper Catalysis with Phenol-NHC Chiral Ligands: A Case of Allylic Coupling with Organoboron Reagents2018

    • Author(s)
      Yuto Yasuda, Hirohisa Ohmiya, Masaya Sawamura
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] キラルプロリノール-ホスフィン-イリジウム触媒によるケトンの水素移動型不斉還元2018

    • Author(s)
      村山大明, 澤村正也
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Transfer Hydrogenation of Alkenes Using 1,4-Dioxane as a Hydrogen Source Catalyzed by a Polystyrene-Cross-Linking Bisphosphine-Iridium Complex2018

    • Author(s)
      Deliang Zhang, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ポリスチレン架橋ビスホスフィン-ニッケル触媒による有機リチウム化合物のクロスカップリング2018

    • Author(s)
      有馬望, 岩井智弘, 澤村正也
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] トリアリールメタン-モノホスフィン:合成、配位特性およびPd触媒共役付加反応への適用2017

    • Author(s)
      岩井 智弘・田中 遼太郎・澤村 正也
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] A Phosphine Cross-Linked Method for Producing Highly Active Heterogeneous Transition Metal Catalysts2017

    • Author(s)
      Tomohiro Iwai, Tomoya Harada, Hajime Shimada, Kiichi Asano, Deliang zhang, Shigenori Chiba, Masaya Sawamura
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ニッケル触媒によるフッ化アリールと第一級アミンのクロスカップリング反応2017

    • Author(s)
      原田 友哉・岩井 智弘・澤村 正也
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Palladium-Catalyzed Enantioselective Side Chain C(α) Allylation of 2-Alkylazaarenes2017

    • Author(s)
      Ryo Murakami, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ボレート含有かご型トリアリールホスフィンの合成と配位特性2017

    • Author(s)
      小西 菖太・岩井 智弘・澤村 正也
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ニッケル触媒とポリスチレン架橋ビスホスフィン配位子を用いる芳香族カルバメートの脱炭酸アミノ化反応2017

    • Author(s)
      鳶巣 守・西澤 彰宏・高比良 剛・岩井 智弘・澤村正也・茶谷直人
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ポリマー架橋型ビスホスフィン配位子を用いた単純芳香族化合物のC-H結合カルボキシル化反応の開発2017

    • Author(s)
      齋藤崇伸・鷹谷絢・浅野輝一・千葉成倫・岩井智弘・澤村正也・岩澤伸治
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Cu-catalyzed Asymmetric Direct Allylic Alkylation of Terminal Alkynes and Azoles: Mechanism and Construction of Quaternary Stereogenic Centers2017

    • Author(s)
      Masaya Sawamura, Hirohisa Ohmiya, Guixiang Zeng, Satoshi Maeda, Tetsuya Taketsugu
    • Organizer
      Pure and Applied Chemistry International Conference 2017(PACCON 2017)
    • Place of Presentation
      Green Convergence on Chemical Frontier(Bangkok, Thailand)
    • Year and Date
      2017-02-02
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 配位子つくって30年2017

    • Author(s)
      澤村正也
    • Organizer
      近畿化学協会有機金属部会 平成29年度第2回例会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Organometallic Catalysis with Polystyrene-Cross-Linking Phosphines2017

    • Author(s)
      Masaya Sawamura
    • Organizer
      The 19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS19)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalytic Enantioselective C(sp3)-H Borylation Reactions using Chiral Monophosphine Ligands2017

    • Author(s)
      Ronald L. Reyes, Tomoya Harada, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      第29回 万有札幌シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Copper-catalyzed Asymmetric Allylic Substitution Reactions with Boron and Silicon Reagents2017

    • Author(s)
      Masaya Sawamura
    • Organizer
      International Conference on Phosphorus, Boron and Silicon
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] キラルモノホスフィン配位子を用いた触媒的不斉 C(sp3)-H ホウ素化反応2017

    • Author(s)
      Ronald L. Reyes, 原田友哉, 岩井智弘, 澤村正也
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 塩基フリーパラジウム触媒による 2-アルキルピリ ジンの不斉 C(sp3)-H アリル化反応2017

    • Author(s)
      村上遼, 佐野建太郎, 岩井智弘, 澤村正也
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ニッケル触媒とポリスチレン架橋ビスホスフィン配位子を用いる芳香族カルバメートの脱炭酸アミノ化反応2017

    • Author(s)
      鳶巣守, 西澤彰宏, 高比良剛, 岩井智弘, 澤村正也, 茶谷直人
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 第一級アミンによるフッ化アリールのニッケル触媒アミノ化反応2017

    • Author(s)
      岩井智弘, 原田友哉, 澤村正也
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 配位子設計が拓いた新しい有機合成2017

    • Author(s)
      澤村正也
    • Organizer
      第34回有機合成化学セミナー,
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Theoretical Studies on Pd-Catalyzed Enantioselective Direct Allylation of 2-Alkylpyridines at the Side Chain α-Position2017

    • Author(s)
      Kyohei Kawashima, Ryo Murakami, Kentaro Sano, Tomohiro Iwai, Masaya Sawamura, Seiji Mori
    • Organizer
      錯体化学会第67回討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ポリスチレン架橋ホスフィン配位子による有機金属触媒反応場の構築2017

    • Author(s)
      澤村正也
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 固定化ホスフィンによる触媒デザイン2017

    • Author(s)
      澤村正也
    • Organizer
      第7回CSJ化学フェスタ, JST特別企画:ACT-Cプログラムが生み出す未来の化学技術
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 銅触媒不斉アルキンーニトロンカップリングによるβ-ラクタムの不斉合成2017

    • Author(s)
      今井洸児・高山ゆりえ・石井孝興, 大宮寛久, 岩井智弘, Schwarzer Martin, 佐藤丈弘, 森聖治, 澤村正也
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Catalytic Asymmetric Heteroatom-Directed C(sp3)-H Borylation with Chiral Monophosphine Ligands2017

    • Author(s)
      Ronald L. Reyes, Tomoya Harada, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      The 12th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Organometallic Catalysis with Polystyrene-Cross-Link Phosphines2017

    • Author(s)
      Masaya Sawamura
    • Organizer
      1st Singapore Japan Germany Trilateral Symposium on Precision Synthesis & Catalysis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Ligand Design for Efficient Organic Synthesis2017

    • Author(s)
      澤村 正也
    • Organizer
      第22回名古屋メダルセミナー
    • Place of Presentation
      名古屋大学(愛知県・名古屋市)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cu-catalyzed Asymmetric Direct Allylic Alkylation of Terminal Alkynes and Azoles: Studies with Phenol-Carbene Chiral Ligands2016

    • Author(s)
      Masaya Sawamura
    • Organizer
      The 11th Internatiuonal Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Korea(Daejeon)
    • Year and Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A Polystyrene-cross-linking Bisphosphine. Synthesis, Properties, and Application to C-O Activation Ni Catalysis2016

    • Author(s)
      Masaya Sawamura
    • Organizer
      International Symposium on C-O Activation
    • Place of Presentation
      姫路商工会議所(兵庫県・姫路市)
    • Year and Date
      2016-10-25
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Creation of Highly Active First-Row Transition Metal Catalysts Based on Coordination Abilities of a Polystyrene-Cross-Linking Bisphosphine2016

    • Author(s)
      Tomohiro Iwai, Tomoya Harada, Hajime Shimada, Kiichi Asano, Masaya Sawamura
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学(東京都・新宿区)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] ポリスチレン架橋ビスホスフィン:第一周期遷移金属触媒における顕著なポリマー効果2016

    • Author(s)
      原田 友哉・岩井 智弘・島田 肇・浅野 輝一・澤村 正也
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      ヒルトンニセコビレッジ(北海道ニセコ町)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of New Solid-immobilized Phosphines for Solving Problems in Organic Synthesis2016

    • Author(s)
      Masaya Sawamura
    • Organizer
      21st International Conference on Phosphorus Chemistry
    • Place of Presentation
      Russia(Kazan)
    • Year and Date
      2016-06-05
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Site-isolation of Phosphine Ligands through Solid-Immobilization : Impact on Activity and Selectivity in Transition Mental Catalysis2016

    • Author(s)
      Masaya Sawamura
    • Organizer
      Peking University & Hokkaido University joint Seminar on Organic Chemistry and Chemical Biology
    • Place of Presentation
      China(Peking)
    • Year and Date
      2016-05-26
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 第一級アルキルアミンによる塩化アリール類のニッケル触媒アミノ化反応:ビスホスフィン分岐ポリスチレンの効果2016

    • Author(s)
      島田 肇
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都府京田辺市, 同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 半中空トリエチニルホスフィン-金触媒を用いた1,9-エンイン類の環化異性化反応による八員環形成2016

    • Author(s)
      上野 将寛
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都府京田辺市, 同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Phosphine-branched Polystyrenes as Platforms for Creating Highly Active Metal Catalysts2016

    • Author(s)
      澤村 正也
    • Organizer
      4th Frontier Chemistry Center International Symposium
    • Place of Presentation
      北海道大学 フロンティア応用科学研究棟(北海道、札幌市)
    • Year and Date
      2016-02-23
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Phosphine-cross-linked Polystyrenes: Application to Ni-catalyzed Amination of Chloroarenes2016

    • Author(s)
      澤村 正也
    • Organizer
      Pure and Applied Chemistry International Conference 2016(PACCON 2016)
    • Place of Presentation
      タイ, バンコック
    • Year and Date
      2016-02-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 固相担持法による高活性遷移金属錯体の創製2016

    • Author(s)
      澤村 正也
    • Organizer
      文部科学省新学術領域研究「高難度物質変換反応の開発を指向した精密制御反応場の創出」第一回公開シンポジウム
    • Place of Presentation
      東京都目黒区, 東工大蔵前会館 くらまえホール
    • Year and Date
      2016-01-30
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 化学のパイオニアを目指して:反応と触媒の設計、合成、発見、イノベーション2016

    • Author(s)
      澤村 正也
    • Organizer
      北海道大学理学部化学同窓会「るつぼ」セミナー
    • Place of Presentation
      北海道大学(北海道・札幌市)
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Medium-ring-forming Gold-catalyzed Alkyne Cyclization Enabled by Hollow-shaped Phosphine Ligands2016

    • Author(s)
      Masaya Sawamura
    • Organizer
      JST-NTU Joint Seminar on Sustainable Synthesis and Catalysis
    • Place of Presentation
      Nangyang Technological University(Singapore, Singapore)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Phosphine-cross-linked polystyrenes as platforms for producing C-H functionalization catalysts (Application of C-H Functionalization)2015

    • Author(s)
      澤村 正也
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      Hawaii, Honolulu(アメリカ)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Phosphine-cross-linked polystyrenes as platforms for producing highly active heterogeneous transition metal catalysts (Nanomaterials as Catalysts for Green Chemistry)2015

    • Author(s)
      澤村 正也
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      Hawaii, Honolulu(アメリカ)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Construction of Medium-sized Rings through Gold(I)-catalyzed Alkyne Cyclizations with Hollow-shaped Phosphine Ligands2015

    • Author(s)
      岩井 智弘
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      Hawaii, Honolulu(アメリカ)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新規固相担持法に基づく高活性金属錯体触媒の開発2015

    • Author(s)
      澤村 正也
    • Organizer
      日産化学株式会社学術講演会
    • Place of Presentation
      千葉県船橋市, 日産化学工業株式会社 物質科学研究所
    • Year and Date
      2015-11-26
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 新規固相担持法に基づく高活性金属錯体触媒の開発2015

    • Author(s)
      澤村 正也
    • Organizer
      第108回有機合成シンポジウム
    • Place of Presentation
      東京都, 新宿区、早稲田大学
    • Year and Date
      2015-11-05
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Ni-Catalyzed Amination of Chloroarenes: Solving Problems with Polystyrene-Bisphosphine Hybrid Ligands2015

    • Author(s)
      澤村 正也
    • Organizer
      The 10th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      台湾、高雄
    • Year and Date
      2015-11-02
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Remarks] 北海道大学大学院理学研究院化学部門 有機金属化学研究室 ホームページ

    • URL

      https://wwwchem.sci.hokudai.ac.jp/~orgmet/

    • Related Report
      2019 Annual Research Report
  • [Remarks] Organometallic Chemistry Lab. Home Page

    • URL

      https://wwwchem.sci.hokudai.ac.jp/~orgmet/index.php?id=25

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report 2017 Annual Research Report
  • [Remarks] 北海道大学大学院理学研究院化学部門 有機金属化学研究室 ホームページ

    • URL

      https://wwwchem.sci.hokudai.ac.jp/~orgmet/

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report
  • [Patent(Industrial Property Rights)] 新規な多孔性架橋ポリマー、それを用いた固定化触媒および装置2020

    • Inventor(s)
      松本光,三浦佳子,星野友,澤村正也,岩井智弘,石川真一
    • Industrial Property Rights Holder
      松本光,三浦佳子,星野友,澤村正也,岩井智弘,石川真一
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2020-031870
    • Filing Date
      2020
    • Related Report
      2019 Annual Research Report

URL: 

Published: 2015-07-02   Modified: 2022-11-04  

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