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Asymmetric Borylation with Chiral Dense Reaction Space

Research Project

Project/Area Number 18H03907
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionHokkaido University

Principal Investigator

Ito Hajime  北海道大学, 工学研究院, 教授 (90282300)

Co-Investigator(Kenkyū-buntansha) 関 朋宏  静岡大学, 理学部, 講師 (50638187)
前田 理  北海道大学, 理学研究院, 教授 (60584836)
百合野 大雅  北海道大学, 工学研究院, 助教 (20771504)
Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥44,200,000 (Direct Cost: ¥34,000,000、Indirect Cost: ¥10,200,000)
Fiscal Year 2021: ¥9,880,000 (Direct Cost: ¥7,600,000、Indirect Cost: ¥2,280,000)
Fiscal Year 2020: ¥9,620,000 (Direct Cost: ¥7,400,000、Indirect Cost: ¥2,220,000)
Fiscal Year 2019: ¥9,880,000 (Direct Cost: ¥7,600,000、Indirect Cost: ¥2,280,000)
Fiscal Year 2018: ¥14,820,000 (Direct Cost: ¥11,400,000、Indirect Cost: ¥3,420,000)
Keywords不斉合成 / 光学活性配位子 / ホウ素化 / 計算化学 / 反応経路自動探索法
Outline of Final Research Achievements

Aiming to establish a new guideline for catalyst development in asymmetric synthetic reactions, this study successfully developed catalysts that can precisely control the selectivity of reaction substrates based on the concept of "asymmetric tight-lattice reaction space". Based on the QuinoxP* ligand, the substituent pattern on phosphorus was successfully designed with the aid of computational chemistry. We also reported a novel approach to control the steric environment by introducing silicon substituents into the backbone. We also succeeded in synthesizing many new optically active organoboron compounds, and developed mechanochemical synthesis.

Academic Significance and Societal Importance of the Research Achievements

光学活性有機ホウ素化合物は、医薬品や機能材料などの開発に極めて重要な化合物であり、世界的に活発な研究がなされている。本研究では、資源として豊富でかつ安価な、シンプルな化合物(末端アルケン、非対称アルケン、芳香族化合物)から、高価値な光学活性有機ホウ素化合物を触媒的に合成する方法を開拓した。また、触媒の設計原理について、「非対称稠密反応空間」という新しい指針を導入することで、これまでに構築することができなかった高度な反応を開発することができた。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (105 results)

All 2022 2021 2020 2019 2018 Other

All Int'l Joint Research (2 results) Journal Article (40 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 40 results,  Open Access: 9 results) Presentation (61 results) (of which Int'l Joint Research: 21 results,  Invited: 19 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Int'l Joint Research] Boston College(米国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] ボストン大学(米国)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems2022

    • Author(s)
      Gao Yunpeng、Feng Chi、Seo Tamae、Kubota Koji、Ito Hajime
    • Journal Title

      Chemical Science

      Volume: 13 Issue: 2 Pages: 430-438

    • DOI

      10.1039/d1sc05257h

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Solid‐State C-N Cross‐Coupling Reactions with Carbazoles as Nitrogen Nucleophiles Using Mechanochemistry2021

    • Author(s)
      Kubota Koji、Endo Tsubura、Uesugi Minami、Hayashi Yuta、Ito Hajime
    • Journal Title

      ChemSusChem

      Volume: 15 Issue: 2

    • DOI

      10.1002/cssc.202102132

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry2021

    • Author(s)
      Takahashi Rikuro、Seo Tamae、Kubota Koji、Ito Hajime
    • Journal Title

      ACS Catalysis

      Volume: 11 Issue: 24 Pages: 14803-14810

    • DOI

      10.1021/acscatal.1c03731

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis2021

    • Author(s)
      Takahashi Rina、Hu Anqi、Gao Pan、Gao Yunpeng、Pang Yadong、Seo Tamae、Jiang Julong、Maeda Satoshi、Takaya Hikaru、Kubota Koji、Ito Hajime
    • Journal Title

      Nature Communications

      Volume: 12 Issue: 1 Pages: 6691-6691

    • DOI

      10.1038/s41467-021-26962-w

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Regio- and Stereoselective Synthesis of Multi-Alkylated Allylic Boronates through Three-Component Coupling Reactions between Allenes, Alkyl Halides, and a Diboron Reagent2021

    • Author(s)
      Ozawa Yu、Endo Kohei、Ito Hajime
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 34 Pages: 13865-13877

    • DOI

      10.1021/jacs.1c06538

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of hydrosilylboronates via the monoborylation of a dihydrosilane Si?H bond and their application for the generation of dialkylhydrosilyl anions2021

    • Author(s)
      Takeuchi Takumi、Shishido Ryosuke、Kubota Koji、Ito Hajime
    • Journal Title

      Chemical Science

      Volume: 12 Issue: 35 Pages: 11799-11804

    • DOI

      10.1039/d1sc01440d

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of Chiral α-Amino Tertiary Boronates via the Catalytic Enantioselective Nucleophilic Borylation of Dialkyl Ketimines2021

    • Author(s)
      Kubota Koji、Miura Daiyo、Takeuchi Takumi、Osaki Shun、Ito Hajime
    • Journal Title

      ACS Catalysis

      Volume: 11 Issue: 11 Pages: 6733-6740

    • DOI

      10.1021/acscatal.1c01689

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Introduction of a Luminophore into Generic Polymers via Mechanoradical Coupling with a Prefluorescent Reagent2021

    • Author(s)
      Kubota Koji、Toyoshima Naoki、Miura Daiyo、Jiang Julong、Maeda Satoshi、Jin Mingoo、Ito Hajime
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 29 Pages: 16003-16008

    • DOI

      10.1002/anie.202105381

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Backbone-Modified <i>C</i><sub>2</sub>-Symmetrical Chiral Bisphosphine TMS-QuinoxP*: Asymmetric Borylation of Racemic Allyl Electrophiles2021

    • Author(s)
      Iwamoto Hiroaki、Ozawa Yu、Takenouchi Yuta、Imamoto Tsuneo、Ito Hajime
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 17 Pages: 6413-6422

    • DOI

      10.1021/jacs.0c08899

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(I)-catalyzed Stereoselective Silylative Dearomatization of Indoles and Pyrroles Using Silylboronates2021

    • Author(s)
      Hayama Keiichi、Takahashi Rikuro、Kubota Koji、Ito Hajime
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 2 Pages: 289-292

    • DOI

      10.1246/cl.200725

    • NAID

      130007986387

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Copper(I)-Catalyzed Radical-Relay Reaction Enabling the Intermolecular 1,2-Alkylborylation of Unactivated Olefins2021

    • Author(s)
      Akiyama Sota、Oyama Natsuki、Endo Tsubura、Kubota Koji、Ito Hajime
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 13 Pages: 5260-5268

    • DOI

      10.1021/jacs.1c02050

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by in Situ Crystallization2020

    • Author(s)
      Seo Tamae、Kubota Koji、Ito Hajime
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 22 Pages: 9884-9889

    • DOI

      10.1021/jacs.0c01739

    • NAID

      120007042003

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] General Synthesis of Trialkyl- and Dialkylarylsilylboranes: Versatile Silicon Nucleophiles in Organic Synthesis2020

    • Author(s)
      Shishido, R.; Uesugi, M.; Takahashi, Rikuro.; Mita, T.; Ishiyama, T.; Kubota, K.; Ito, H.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 142 Issue: 33 Pages: 1412514133-1412514133

    • DOI

      10.1021/jacs.0c03011

    • NAID

      120007132047

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid‐State Radical C-H Trifluoromethylation Reactions Using Ball Milling and Piezoelectric Materials2020

    • Author(s)
      Pang Yadong、Lee Joo Won、Kubota Koji、Ito Hajime
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 59 Issue: 50 Pages: 22570-22576

    • DOI

      10.1002/anie.202009844

    • NAID

      120007175161

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Glove-Box- and Schlenk-Line-Free Protocol for Solid-State C-N Cross-Coupling Reactions Using Mechanochemistry2020

    • Author(s)
      Kubota Koji、Takahashi Rikuro、Uesugi Minami、Ito Hajime
    • Journal Title

      ACS Sustainable Chemistry & Engineering

      Volume: 8 Issue: 44 Pages: 16577-16582

    • DOI

      10.1021/acssuschemeng.0c05834

    • NAID

      120007171677

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Encapsulating N-Heterocyclic Carbene Binuclear Transition-Metal Complexes as a New Platform for Molecular Rotation in Crystalline Solid-State2020

    • Author(s)
      Jin Mingoo、Ando Rempei、Jellen Marcus J.、Garcia-Garibay Miguel A.、Ito Hajime
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 2 Pages: 1144-1153

    • DOI

      10.1021/jacs.0c11981

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Crystal Jumping of Simple Hydrocarbons: Cooling-induced Salient Effect of Bis-, Tri-, and Tetraphenylethene through Anisotropic Lattice Dimension Changes without Thermal Phase Transitions2020

    • Author(s)
      Seki Tomohiro、Mashimo Takaki、Ito Hajime
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 2 Pages: 174-177

    • DOI

      10.1246/cl.190768

    • NAID

      130007795065

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis and Tunable Optical Properties of C,N‐Chelated Borate Luminophores Derived from Potassium Acyltrifluoroborates2020

    • Author(s)
      Taguchi Jumpei、Matsuura Satsuki、Seki Tomohiro、Ito Hajime
    • Journal Title

      Chemistry A European Journal

      Volume: 26 Issue: 11 Pages: 2450-2455

    • DOI

      10.1002/chem.201904983

    • NAID

      120006960650

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral N-Heterocyclic Allylboronates via the Enantioselective Borylative Dearomatization of Pyrroles2020

    • Author(s)
      Hayama Keiichi、Kojima Ryoto、Kubota Koji、Ito Hajime
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 2 Pages: 739-744

    • DOI

      10.1021/acs.orglett.9b04581

    • NAID

      120006953323

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Silyl-Group-Directed Linear-Selective Allylation of Carbonyl Compounds with Trisubstituted Allylboronates Using a Copper(I) Catalyst2020

    • Author(s)
      Iwamoto Hiroaki、Hayashi Yuta、Ozawa Yu、Ito Hajime
    • Journal Title

      ACS Catalysis

      Volume: 10 Issue: 4 Pages: 2471-2476

    • DOI

      10.1021/acscatal.9b05408

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mixed crystal formation of two gold isocyanide complexes with various ratios for continuous tuning of photophysical properties2020

    • Author(s)
      Seki Tomohiro、Toyoshima Naoki、Ito Hajime
    • Journal Title

      Dalton Transactions

      Volume: 49 Issue: 7 Pages: 2073-2076

    • DOI

      10.1039/d0dt00195c

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(I)-Catalyzed Boryl Substitution of 1-Trifluoromethyl Allenes for the Synthesis of 3-Boryl-Substituted 1,1-gem-Difluorodienes2020

    • Author(s)
      Akiyama Sota、Nomura Syogo、Kubota Koji、Ito Hajime
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 85 Issue: 6 Pages: 4172-4181

    • DOI

      10.1021/acs.joc.9b03353

    • NAID

      120006978440

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Luminescent mechanochromism of gold N-heterocyclic carbene complexes with hypso- and bathochromic spectral shifts2019

    • Author(s)
      Seki Tomohiro、Kashiyama Kentaro、Ito Hajime
    • Journal Title

      Dalton Transactions

      Volume: 印刷中 Issue: 21 Pages: 7105-7109

    • DOI

      10.1039/c9dt00566h

    • NAID

      120006849864

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 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)2019

    • Author(s)
      Kubota Koji、Takahashi Rina、Ito Hajime
    • Journal Title

      Chemical Science

      Volume: 10 Issue: 22 Pages: 5837-5842

    • DOI

      10.1039/c9sc01711a

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of 2-alkyl-2-boryl-substituted-tetrahydrofurans via copper(i)-catalysed borylative cyclization of aliphatic ketones2019

    • Author(s)
      Kubota Koji、Uesugi Minami、Osaki Shun、Ito Hajime
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 17 Issue: 23 Pages: 5680-5683

    • DOI

      10.1039/c9ob00962k

    • NAID

      120006863167

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(I)‐Catalyzed Enantioconvergent Borylation of Racemic Benzyl Chlorides Enabled by Quadrant‐by‐Quadrant Structure Modification of Chiral Bisphosphine Ligands2019

    • Author(s)
      Iwamoto Hiroaki、Endo Kohei、Ozawa Yu、Watanabe Yuta、Kubota Koji、Imamoto Tsuneo、Ito Hajime
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 32 Pages: 11112-11117

    • DOI

      10.1002/anie.201906011

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives2019

    • Author(s)
      Akiyama Sota、Kubota Koji、Mikus Malte S.、Paioti Paulo H. S.、Romiti Filippo、Liu Qinghe、Zhou Yuebiao、Hoveyda Amir H.、Ito Hajime
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 35 Pages: 11998-12003

    • DOI

      10.1002/anie.201906283

    • NAID

      120006880722

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Olefin-accelerated C-C cross-coupling reaction in solid-state2019

    • Author(s)
      Seo, T.; Ishiyama, T.; Kubota, K.; Ito, H.
    • Journal Title

      Chem. Sci.

      Volume: 10 Issue: 35 Pages: 8202-8210

    • DOI

      10.1039/c9sc02185j

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] The Direct Dimesitylborylation of Benzofuran Derivatives via an Iridium-Catalyzed C-H Activation with Silyldimesitylborane2019

    • Author(s)
      Shishido, R.; Sasaki, I.; Seki, T.; Ishiyama, T.; Ito, H.*
    • Journal Title

      Chem. Eur. J.

      Volume: 25 Issue: 56 Pages: 12924-12928

    • DOI

      10.1002/chem.201903776

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Anisotropic Thermal Expansion as the Source of Macroscopic and Molecular Scale Motion in Phosphorescent Amphidynamic Crystals2019

    • Author(s)
      Jin Mingoo、Yamamoto Sho、Seki Tomohiro、Ito Hajime、Garcia‐Garibay Miguel A.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 50 Pages: 18003-18010

    • DOI

      10.1002/anie.201909048

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Redox reactions of small organic molecules using ball milling and piezoelectric materials2019

    • Author(s)
      Kubota Koji、Pang Yadong、Miura Akira、Ito Hajime
    • Journal Title

      Science

      Volume: 366 Issue: 6472 Pages: 1500-1504

    • DOI

      10.1126/science.aay8224

    • NAID

      120006781563

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Aurophilicity‐Mediated Construction of Emissive Porous Molecular Crystals as Versatile Hosts for Liquid and Solid Guests2019

    • Author(s)
      Seki Tomohiro、Ida Kentaro、Sato Hiroyasu、Aono Shinji、Sakaki Shigeyoshi、Ito Hajime
    • Journal Title

      Chemistry A European Journal

      Volume: 26 Issue: 3 Pages: 735-744

    • DOI

      10.1002/chem.201904597

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Olefin-accelerated solid-state C-N cross-coupling reactions using mechanochemistry2019

    • Author(s)
      Kubota Koji、Seo Tamae、Koide Katsumasa、Hasegawa Yasuchika、Ito Hajime
    • Journal Title

      Nature Communications

      Volume: 10 Issue: 1 Pages: 111-122

    • DOI

      10.1038/s41467-018-08017-9

    • NAID

      120006585972

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Iridium(I)‐Catalyzed C-H Borylation in Air by Using Mechanochemistry2019

    • Author(s)
      Pang Yadong、Ishiyama Tatsuo、Kubota Koji、Ito Hajime
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 18 Pages: 4654-4659

    • DOI

      10.1002/chem.201900685

    • NAID

      120006823180

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Concise Synthesis of Potassium Acyltrifluoroborates from Aldehydes through Copper(I)-Catalyzed Borylation/Oxidation2019

    • Author(s)
      Taguchi Jumpei、Takeuchi Takumi、Takahashi Rina、Masero Fabio、Ito Hajime
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 22 Pages: 7299-7303

    • DOI

      10.1002/anie.201901748

    • NAID

      120006846276

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(I)-catalysed regio- and diastereoselective intramolecular alkylboration of terminal allenes via allylcopper(i) isomerization2018

    • Author(s)
      Ozawa Yu、Iwamoto Hiroaki、Ito Hajime
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 39 Pages: 4991-4994

    • DOI

      10.1039/c8cc02692k

    • NAID

      120006628676

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Copper(I)-Catalyzed Enantioselective γ-Boryl Substitution of Trifluoromethyl-Substituted Alkenes: Synthesis of Enantioenriched γ,γ-gem-Difluoroallylboronates2018

    • Author(s)
      Kojima Ryoto、Akiyama Sota、Ito Hajime
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 24 Pages: 7196-7199

    • DOI

      10.1002/anie.201803663

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Computational design of high-performance ligand for enantioselective Markovnikov hydroboration of aliphatic terminal alkenes2018

    • Author(s)
      Iwamoto Hiroaki、Imamoto Tsuneo、Ito Hajime
    • Journal Title

      Nature Communications

      Volume: 9 Issue: 1 Pages: 2290-2300

    • DOI

      10.1038/s41467-018-04693-9

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Copper(I)-catalyzed Stereoselective Defluoroborylation of Aliphatic Gem-Difluoroalkenes2018

    • Author(s)
      Ito Hajime、Seo Tamae、Kojima Ryoto、Kubota Koji
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 10 Pages: 1330-1332

    • DOI

      10.1246/cl.180656

    • NAID

      130007496129

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(I)-catalysed stereoselective debromoborylation of aliphatic 1,1-dibromo-1-alkenes with bis(pinacolato)diboron2018

    • Author(s)
      Pang Yadong、Kojima Ryoto、Ito Hajime
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 16 Issue: 34 Pages: 6187-6190

    • DOI

      10.1039/c8ob01778f

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] 銅(I)およびパラジウム(II)触媒を用いたgem-二置換アレン類のカルボホウ素化反応の開発2022

    • Author(s)
      小澤 友、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] アレン類のアルキルホウ素化反応による四置換アルケニルホウ素化合物の立体選択的な合成2022

    • Author(s)
      白鳥 友万、小澤 友、遠藤 康平、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] アリル求電子剤に対する速度論的光学分割によるγ位不斉ホウ素化反応2022

    • Author(s)
      高橋 陸朗、小澤 友、岩本 紘明、今本 恒雄、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Computer-Assisted Reaction Design for Copper-Catalyzed Borylation2022

    • Author(s)
      Hajime Ito
    • Organizer
      4th ICReDD International Symposium
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] General synthesis of trialkylsilylboranes and their use as silicon nucleophiles2021

    • Author(s)
      Koi Kubota, Ryosuke Shishido, Minami Uesugi, Rikuro Takahashi, Tsuyoshi Miya, Tatsuo Ishiyama, Hajime Ito
    • Organizer
      The 2021 International Chemical Congress of Pacific Basin Societies
    • Related Report
      2021 Annual Research Report
  • [Presentation] Reactivity and Enantioselectivity Improvement of Copper(I)-Catalyzed γ-Borylation Reaction of Racemic Allyl Electrophiles2021

    • Author(s)
      Yu Ozawa, Hiroaki Iwamoto, Yuta Takenouchi, Tsuneo Imamoto, Hajime Ito
    • Organizer
      The 2021 International Chemical Congress of Pacific Basin Societies
    • Related Report
      2021 Annual Research Report
  • [Presentation] Computer-Aided Reaction Design for Asymmetric Cu(I)-catalyzed Borylation2021

    • Author(s)
      Hajime Ito
    • Organizer
      3rd Chinese Chemical Society Conference on Boron Science (CCS-CBS)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 炭素ーホウ素およびケイ素ーホウ素結合を持つ化合物の合成と反応2021

    • Author(s)
      伊藤 肇
    • Organizer
      東京大学 化学生命工学専攻 第14回ハイブリットレクチャー
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] ジヒドロシランのモノホウ素化反応によるヒドロシリルボロネートの合成2021

    • Author(s)
      竹内 拓未・宍戸 亮介・久保田 浩司・伊藤 肇
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 銅(I)触媒による全炭素四置換アルケン構造を有するアリルホウ素化合物の立体選択的合成2021

    • Author(s)
      小澤 友・遠藤 康平・伊藤 肇
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] シリルホウ素化合物の新しい合成法と幅広いケイ素求核剤の発生2021

    • Author(s)
      伊藤肇
    • Organizer
      ケイ素化学協会 オンライン講演会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 1,1-二置換アレン類のアルキルホウ素化反応による多置換アリルホウ素化合物の位置および立体選択的合成2021

    • Author(s)
      小澤 友、遠藤 康平、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 塩基性条件下に不安定なアリルーボロン酸を用いたメカノケミカルクロスカップリング2021

    • Author(s)
      高橋 陸朗、瀬尾 珠恵、久保田 浩司、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ジヒドロシランのSi-Hモノホウ素化によるヒドロシリルボランの合成2021

    • Author(s)
      竹内 拓未、宍戸 亮介、久保田 浩司、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] メカノケミストリーによる不溶性アリールハライドの固体クロスカップリング反応2021

    • Author(s)
      瀬尾 珠恵、豊島 直喜、久保田 浩司、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] メカノレドックスによるC-H官能基化反応2021

    • Author(s)
      YADONG PANG、JOO WON LEE、久保田 浩司、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 銅(I)触媒を用いたラジカルリレー機構によるオレフィンの分子間1,2-カルボホウ素化反応の開発2021

    • Author(s)
      秋山 颯太、大山 夏生、遠藤 円、久保田 浩司、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 無溶媒メカノケミカル合成による炭素求核剤として働く有機マグネシウム試薬の合成と有機合成への応用2021

    • Author(s)
      高橋 里奈、Anqi Hu、Yadong Pang 、瀬尾 珠恵、久保田 浩司、伊藤 肇
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Experimental Reaction Developments with Power of Computation2021

    • Author(s)
      Hajime Ito
    • Organizer
      3rd ICReDD International Symposium
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] メカノケミカル合成の夜明け2020

    • Author(s)
      伊藤肇
    • Organizer
      ケムステバーチャルシンポジウム【最先端有機化学】
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] In Situ Crystallization Enables Selective Monoarylation of Dibromoarenes2020

    • Author(s)
      Tamae Seo, Koji Kubota, Hajime Ito
    • Organizer
      The 6.5th Crystal Engineering and Emerging Materials Workshop of Ontario and Quebec
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Ball-Mill Organic Synthesis: Mechanoredox and Solid State Cross-Coupling2020

    • Author(s)
      Hajime Ito
    • Organizer
      Department Webmnar, Indian Institute of Science Education and Research (IISER)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 三象限遮蔽型不斉ビスホスフィン配位子/銅(I)触媒系を用いたエナンチオ収束的ホウ素化反応の開発2020

    • Author(s)
      遠藤 康平・岩本 紘明・小澤 友・渡邉 裕太・久保田 浩司・今本 恒雄・伊藤 肇
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] 脂肪族ケチミン類のホウ素化による光学活性第三級α-アミノボロン酸誘導体の触媒的不斉合成2020

    • Author(s)
      三浦 大洋・竹内 拓未・大崎 峻・久保田 浩司・伊藤 肇
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] 空気下で簡便に実施可能な固体C-Nクロスカップリング反応2020

    • Author(s)
      高橋 陸朗・上杉 実那美・久保田 浩司・伊藤 肇
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] メカノケミカル有機合成の夜明け2020

    • Author(s)
      伊藤肇
    • Organizer
      MRMforum2020 TS-5 動的分子アーキテクトニクス
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] シリルボランの新しい合成法と有機ケイ素求核反応への応用2020

    • Author(s)
      伊藤肇
    • Organizer
      第47回有機典型元素化学討論会 特別講演会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] メカノケミストリーによる固体クロスカップリング反応2020

    • Author(s)
      瀬尾 珠恵・久保田 浩司・伊藤 肇
    • Organizer
      第32回万有札幌シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] Solid-state cross-coupling as a new tool for organic chemistry2020

    • Author(s)
      Hajime Ito
    • Organizer
      Mechanochemistry Virtual Symposium #1
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 非芳香族アミノ酸類縁体分子の固体室温長寿命発光2020

    • Author(s)
      眞下 峻希・田口 純平・関 朋宏・小野 ゆり子・武次 徹也・伊藤 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] トリアルキルシリルボランの新規合成法の開発2020

    • Author(s)
      宍戸 亮介・上杉 実那美・久保田 浩司・伊藤 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 計算化学による直接エナンチオ収束ホウ素化反応の反応機構解析2020

    • Author(s)
      小澤 友・岩本 紘明・竹ノ内 雄太・今本 恒雄・伊藤 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] インドール及びピロールの脱芳香族シリル化反応の開発2020

    • Author(s)
      髙橋 陸朗・羽山 慶一・久保田 浩司・伊藤 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 銅(I)触媒によるピロールの不斉脱芳香族ホウ素化反応の開発2020

    • Author(s)
      羽山 慶一・小島 遼人・久保田 浩司・伊藤 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 銅(l)触媒を用いた脂肪族ケチミン類に対する不斉ホウ素化反応の開発2020

    • Author(s)
      三浦 大洋・竹内 拓未・大崎 駿・久保田 浩司・伊藤 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 計算化学を駆使した配位子デザインによるエチルメチルケトンの不斉ホウ素化2020

    • Author(s)
      竹内 拓未・久保田 浩司・伊藤 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Xantphos-ligated Palladium Dialkyl Complex as an Effective Precatalyst for Cross-coupling Reactions2020

    • Author(s)
      TAKAHASHI, Rina; KUBOTA, Koji; ITO, Hajime
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Copper(I)-Catalyzed Enantioselective Synthesis of Fluorine-Containing Allylic Boronates and their Transformations2020

    • Author(s)
      Sota Akiyama, Koji Kubota, Hajime Ito
    • Organizer
      Nanyang Research Conference Synthetic Chemistry and Catalysis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reactivity and Enantioselectivity Enhancement of Direct Enantioconvergent Borylation by Gear-meshing-like Effect in Phosphorus Ligand2020

    • Author(s)
      Yu Ozawa, Hiroaki Iwamoto, Yuta Takenouchi, Tsuneo Imamoto, Hajime Ito
    • Organizer
      Nanyang Research Conference Synthetic Chemistry and Catalysis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] トリアルキルシリルボラン化合物の一般的合成法の開発2019

    • Author(s)
      宍戸 亮介・上杉 実那美・久保田 浩司・伊藤 肇
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 銅(I)触媒による脱芳香族ホウ素化およびケイ素化2019

    • Author(s)
      久保田 浩司・羽山 慶一・高橋 陸朗・小島 遼人・伊藤 肇
    • Organizer
      第23回ケイ素化学協会シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 新奇トリアルキルシリルボランの合成とシリルアニオン等価体としての利用2019

    • Author(s)
      上杉 実那美・宍戸 亮介・久保田 浩司・伊藤 肇
    • Organizer
      第23回ケイ素化学協会シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Copper(I)-Catalyzed selective Synthesis of Fluorine-Containing Organoboron Compounds and their Applications2019

    • Author(s)
      秋山 颯太
    • Organizer
      第10回大津会議
    • Related Report
      2019 Annual Research Report
  • [Presentation] Copper(I)-catalyzed borylation: the discovery and recent development2019

    • Author(s)
      Hajime Ito
    • Organizer
      Sichuan University Lecture
    • Related Report
      2019 Annual Research Report
  • [Presentation] 銅(I)触媒を用いた光学活性モノフルオロアルケニルアリルホウ素化合物の合成とそれら化合物を応用した含フッ素四級不斉中心の構築2019

    • Author(s)
      秋山 颯太、久保田 浩司、S. Malte Mikus、Paulo H. S. Paioti、Filippo Romiti、Qinghe Liu、Yuebiao Zhou、Amir. H. Hoveyda、伊藤 肇
    • Organizer
      第66回有機金属化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Computer-assisted design of asymmetric copper-catalyzed borylation of terminal aliphatic alkenes2019

    • Author(s)
      Hiroaki Iwamoto, Tsuneo Imamoto, Hajime Ito
    • Organizer
      ACS Fall 2019 National Meeting & Exposition 2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Concise synthesis of potassium acyltrifluoroborartes from aldehydes by borylation and oxidation2019

    • Author(s)
      Takumi Takeuchi, Jumpei Taguchi, Rina Takahashi, Fabio Masero, Hajime Ito
    • Organizer
      ACS Fall 2019 National Meeting & Exposition 2019
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis of Trialkylsilylboranes Through Rh-Catalyzed Borylation of Trialkylsilanes and generation of a Broad Range of Trialkylsilyl Nucleophiles2019

    • Author(s)
      Hajime Ito
    • Organizer
      The 7th Asian Silicon Symposium
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] General Synthesis of Oligosilanes: Rhodium-Catalyzed Si-H Borylation and Silicone- Silicone Coupling Reactuon2019

    • Author(s)
      Ryosuke Shishido, Minami Uesugi, Koji Kubota, Hajime Ito
    • Organizer
      0th Organometallic Catalysis Directed Towards Organic Synthesis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Enantioselective Borylative Dearomatization of Pyroles Using Cu(I) Catalysis2019

    • Author(s)
      Keiichi Hayama, Ryoto Kojima, Koji Kubota, Hajime Ito
    • Organizer
      20th Organometallic Catalysis Directed Towards Organic Synthesis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] アルデヒドのホウ素化と続く酸化によるカリウムアシルトリフルオロボレートの合成2019

    • Author(s)
      竹内 拓未、田口純平、高橋 里奈、Fabio Masero、伊藤 肇
    • Organizer
      第31回万有札幌シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Direct dimesitylborylation of benzofurans via iridium-catalyzed C-H activation with silyldimesitylborane2019

    • Author(s)
      Ryosuke Shishido
    • Organizer
      The 47th Naito Conference on C-H Bond Activation and Transformation
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Copper(I)-Catalyzed Borylation with Diboron: the Beginning and Recent Study2019

    • Author(s)
      Hajime Ito
    • Organizer
      Nanjing University Lecture
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] How do we design new chemical reactions by combining computations and experiments?2019

    • Author(s)
      Hajime Ito
    • Organizer
      1st ICReDD International Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Asymmetric Copper-Catalyzed Borylative Dearomatization: New Pathway to Optically Active Heterocyclic Boron Compounds2018

    • Author(s)
      Hajime Ito
    • Organizer
      4th International Conference on Organometallic and Catalysis 2018(OM&Cat 2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper-Catalyzed Asymmetric Borylative Dearomatization for Optically Active Heterocyclic Compounds2018

    • Author(s)
      Hajime Ito
    • Organizer
      16th Boron Chemistry Meeting in the Americas
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 銅(I)触媒による不斉ホウ素化反応における量子化学計算を駆使した高性能不斉ビスホスフィン配位子の合理的デザイン2018

    • Author(s)
      岩本 紘明・小澤 友・今本 恒雄・伊藤 肇
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Oxidative Synthesis of α-Amino Acylborons and their Application to Peptide Ligation2018

    • Author(s)
      Jumpei Taguchi, Takumi Takeuchi, Rina Takahashi, Jeffrey W. Bode, Hajime Ito
    • Organizer
      The 8th Junior International Conference on Cutting-Edge Organic Chemistry in Asia
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Computer-Assisted Design of P-Chirogenic Ligand for Enantioselective Markovnikov Hydroboration of Aliphatic Terminal Alkenes2018

    • Author(s)
      Hajime Ito
    • Organizer
      The 8th Spanish-Portuguese-Japanese Organic Chemistry Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper(I)-catalyzed borylation: from the early to current study2018

    • Author(s)
      Hajime Ito
    • Organizer
      Lecture at Suzhou Research Institute of LICP
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper(I)-catalyzed borylation: from the early to current study2018

    • Author(s)
      Hajime Ito
    • Organizer
      Lecture at University of Science & Technology of China
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Remarks] 有機元素化学研究室

    • URL

      https://itogrouphp.eng.hokudai.ac.jp/

    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] 2,3-ビスホスフィノピラジン錯体、その製造方法、遷移金属錯体及び不斉触媒並びに有機ホウ素化合物の製造方法2018

    • Inventor(s)
      伊藤肇、岩本紘明、今本恒雄、田村健、佐野夏博
    • Industrial Property Rights Holder
      伊藤肇、岩本紘明、今本恒雄、田村健、佐野夏博
    • Industrial Property Rights Type
      特許
    • Filing Date
      2018
    • Related Report
      2018 Annual Research Report
    • Overseas

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Published: 2018-04-23   Modified: 2023-01-30  

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