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Organic synthesis by means of breaking aromaticity via reduction

Research Project

Project/Area Number 19H00895
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 InstitutionKyoto University

Principal Investigator

Yorimitsu Hideki  京都大学, 理学研究科, 教授 (00372566)

Project Period (FY) 2019-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥45,890,000 (Direct Cost: ¥35,300,000、Indirect Cost: ¥10,590,000)
Fiscal Year 2022: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
Fiscal Year 2021: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
Fiscal Year 2020: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
Fiscal Year 2019: ¥20,540,000 (Direct Cost: ¥15,800,000、Indirect Cost: ¥4,740,000)
Keywords芳香環メタモルフォシス / 還元 / ケミカルスペース / ヘテロール / 芳香環破壊 / 求核置換 / リチオ化
Outline of Research at the Start

頑丈で安定なヘテロ芳香環を還元的に破壊・開裂する新手法を開発し、芳香環の骨格そのものを改変する斬新な有機合成手法を創出する。具体的には、「高反応性求核剤の付加」や「金属リチウムからの電子移動」を鍵素反応として、「ヘテロ芳香環内への原子挿入」や「ヘテロ芳香環内原子の置換」を達成する。これらの革新的手法に基づき、窒素、ケイ素、ホウ素、リンなどを環内鍵元素とする未知の機能を秘めた新規エキゾチックヘテロ芳香族分子群を続々と生み出す。こうして、化学・医農薬・エレクトロニクス産業にまで波及する新しい芳香族化学を切り拓く。

Outline of Final Research Achievements

By utilizing metallic lithium, we have established 1) a method for inserting various atoms, including boron and silicon, into the carbon-nitrogen bond in the indole ring and 2) a simple and convenient method for the synthesis of substituted heteroles such as siloles and phospholes via the corresponding dilithium reagents that are reductively generated from thiophenes.
We have established a method to construct carbazole and seven-membered dibenzoazepine skeletons by the reactions of dibenzothiophene dioxide with alkanamine and N-benzylbenzaldehyde imine, respectively, under basic conditions. Furthermore, the synthesis of a series of heteroatom-containing helicenes by utilizing aromatic ring metamorphosis has been established, which have clarified the usefulness of aromatic ring metamorphosis.

Academic Significance and Societal Importance of the Research Achievements

頑丈で安定なヘテロ芳香環を還元的に破壊・開裂する新手法を開発し、芳香環の骨格そのものを改変する斬新な有機合成手法を数多く創出できた。これらの革新的手法に基づき、窒素、ケイ素、ホウ素、リンなどを環内鍵元素とする未知の機能を秘めた新規エキゾチックヘテロ芳香族分子群を続々と生み出した。化学・医農薬・エレクトロニクス産業にまで波及する新しい芳香族化学の基盤となる。

Report

(6 results)
  • 2023 Final Research Report ( PDF )
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • 2020 Annual Research Report
  • 2019 Comments on the Screening Results   Annual Research Report
  • Research Products

    (116 results)

All 2024 2023 2022 2021 2020 2019 Other

All Int'l Joint Research (4 results) Journal Article (58 results) (of which Int'l Joint Research: 7 results,  Peer Reviewed: 58 results,  Open Access: 11 results) Presentation (49 results) (of which Int'l Joint Research: 18 results,  Invited: 27 results) Remarks (5 results)

  • [Int'l Joint Research] マンチェスター大学(英国)

    • Related Report
      2022 Annual Research Report
  • [Int'l Joint Research] 湖北工業大学(中国)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] 国立台北科技大学(その他の国・地域)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] ICIQ(スペイン)

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Stereo- and regioselective boryllithiation and -sodiation of alkynes: reductive approach using flow microreactors2024

    • Author(s)
      Jiang Yiyuan、Kurogi Takashi、Yorimitsu Hideki
    • Journal Title

      Nature Synthesis

      Volume: 3 Pages: 192-201

    • DOI

      10.21203/rs.3.rs-2687146/v1

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Regioselectivity in the sulfonium-mediated arylation reactions of 2-substituted phenols with benzothienyl sulfoxide2024

    • Author(s)
      Wakabayashi Ryota、Fukazawa Mizuki、Kurogi Takashi、Yorimitsu Hideki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 97 Issue: 1

    • DOI

      10.1093/bulcsj/uoae002

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sodium-Mediated Reductive C-C Bond Cleavage Assisted by Boryl Groups2024

    • Author(s)
      Fukazawa Mizuki、Takahashi Fumiya、Kurogi Takashi、Yorimitsu Hideki
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 19 Issue: 8

    • DOI

      10.1002/asia.202400100

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] [1,2]-Retro-Brook Rearrangement Induced by Electrochemical Reduction of Silyl Enolates2024

    • Author(s)
      Kinoshita Ban、Maejima Saki、Niki Yuta、Mitsudo Koichi、Suga Seiji、Yorimitsu Hideki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: - Issue: 4

    • DOI

      10.1093/bulcsj/uoae038

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Diphenylsilylsilanolates Enable the Transfer of a Wide Range of Silyl Groups2023

    • Author(s)
      Yamagishi Hiroki、Harata Fuyuki、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 25 Issue: 1 Pages: 11-15

    • DOI

      10.1021/acs.orglett.2c03558

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of trans-1,2-dimetalloalkenes through reductive anti-dimagnesiation and dialumination of alkynes2023

    • Author(s)
      Takahashi Fumiya、Kurogi Takashi、Yorimitsu Hideki
    • Journal Title

      Nature Synthesis

      Volume: 2 Issue: 2 Pages: 162-171

    • DOI

      10.1038/s44160-022-00189-z

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Carboxylic Acid Salts as Dual‐Function Reagents for Carboxylation and Carbon Isotope Labeling2023

    • Author(s)
      Wang Shuo、Larrosa Igor、Yorimitsu Hideki、Perry Gregory J. P.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 14

    • DOI

      10.1002/anie.202218371

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Stereoselective Synthesis of Tetraarylethylenes Enabled by Reductive anti‐1,2‐Dimetallation of Alkynes2023

    • Author(s)
      Takahashi Fumiya、Yorimitsu Hideki
    • Journal Title

      Chemistry - A European Journal

      Volume: - Issue: 26

    • DOI

      10.1002/chem.202203988

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of Vinylic Lithium Reagents from Silyl Enolates of Alkyl Aryl Ketones Using Lithium Arenide2023

    • Author(s)
      Zhang Ziwei、Takahashi Fumiya、Kurogi Takashi、Yorimitsu Hideki
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 12 Issue: 7

    • DOI

      10.1002/ajoc.202300242

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aromatic metamorphosis of an indole into 2-quinolone, dihydrobenzazasiline, and dihydrobenzazagermine2023

    • Author(s)
      Nishihara Kazuki、Kurogi Takashi、Yorimitsu Hideki
    • Journal Title

      Arkivoc

      Volume: 2023 Issue: 2 Pages: 202312017-202312017

    • DOI

      10.24820/ark.5550190.p012.017

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Late-stage sulfonic acid/sulfonate formation from sulfonamides via sulfonyl pyrroles2022

    • Author(s)
      Ozaki Tomoya、Yorimitsu Hideki、Perry Gregory J.P.
    • Journal Title

      Tetrahedron

      Volume: 117-118 Pages: 132830-132830

    • DOI

      10.1016/j.tet.2022.132830

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Zincation of Styrylsulfonium Salts2022

    • Author(s)
      Yamada Kodai、Kintzel Mika B.、Perry Gregory J. P.、Saito Hayate、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 40 Pages: 7446-7449

    • DOI

      10.1021/acs.orglett.2c03013

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Taming Highly Unstable Radical Anions and 1,4-Organodilithiums by Flow Microreactors: Controlled Reductive Dimerization of Styrenes2022

    • Author(s)
      Jiang Yiyuan、Yorimitsu Hideki
    • Journal Title

      JACS Au

      Volume: 2 Issue: 11 Pages: 2514-2521

    • DOI

      10.1021/jacsau.2c00375

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Borylation of Alkenyl Carbamates by Means of Sodium Metal2022

    • Author(s)
      Koyama Shunsuke、Takahashi Fumiya、Saito Hayate、Yorimitsu Hideki
    • Journal Title

      Synthesis

      Volume: - Issue: 11 Pages: 1744-1751

    • DOI

      10.1055/a-1970-4584

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reductive Ring Opening of Arylcyclopropanecarboxamides Accompanied by Borylation and Enolate Formation2022

    • Author(s)
      Wang Shuo、Kaga Atsushi、Kurogi Takashi、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 4 Pages: 1105-1109

    • DOI

      10.1021/acs.orglett.2c00084

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sodium silylsilanolate as a precursor of silylcopper species2022

    • Author(s)
      Yamagishi Hiroki、Hitoshio Kenshiro、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      Chemical Science

      Volume: 13 Issue: 15 Pages: 4334-4340

    • DOI

      10.1039/d2sc00227b

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Sulfur(IV) in Transition-Metal-Free Cross-Couplings for Biaryl Synthesis2022

    • Author(s)
      Perry Gregory J. P.、Yorimitsu Hideki
    • Journal Title

      ACS Sustainable Chemistry & Engineering

      Volume: 10 Issue: 8 Pages: 2569-2586

    • DOI

      10.1021/acssuschemeng.1c08673

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Defluorinative Diborasodiation of Benzotrifluorides with Bis(pinacolato)Diboron and Sodium2021

    • Author(s)
      Ito Shiori、Takahashi Fumiya、Yorimitsu Hideki
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 10 Issue: 6 Pages: 1440-1443

    • DOI

      10.1002/ajoc.202100206

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sodium-Promoted Borylation of Polycyclic Aromatic Hydrocarbons2021

    • Author(s)
      Fukazawa Mizuki、Takahashi Fumiya、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 12 Pages: 4613-4617

    • DOI

      10.1021/acs.orglett.1c01355

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The dioxasilepanyl group as a versatile organometallic unit: studies on stability, reactivity, and utility2021

    • Author(s)
      Saito Hayate、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      Chemical Science

      Volume: 12 Issue: 27 Pages: 9546-9555

    • DOI

      10.1039/d1sc02083h

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Generation of Aryllithium Reagents from N-Arylpyrroles Using Lithium2021

    • Author(s)
      Yorimitsu Hideki、Ozaki Tomoya、Kaga Atsushi、Saito Hayate
    • Journal Title

      Synthesis

      Volume: 53 Issue: 17 Pages: 3019-3028

    • DOI

      10.1055/a-1482-2567

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts2021

    • Author(s)
      Yorimitsu Hideki、Minami Hiroko、Nogi Keisuke
    • Journal Title

      Synlett

      Volume: 32 Issue: 15 Pages: 1542-1546

    • DOI

      10.1055/s-0040-1707817

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design, Synthesis, and Implementation of Sodium Silylsilanolates as Silyl Transfer Reagents2021

    • Author(s)
      Yamagishi Hiroki、Saito Hayate、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      ACS Catalysis

      Volume: 11 Issue: 16 Pages: 10095-10103

    • DOI

      10.1021/acscatal.1c02733

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sodium silylsilanolate enables nickel-catalysed silylation of aryl chlorides2021

    • Author(s)
      Hitoshio Kenshiro、Yamagishi Hiroki、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 56 Pages: 6867-6870

    • DOI

      10.1039/d1cc02683f

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mechanistic Investigation of a Synthetic Route to Biaryls by the Sigmatropic Rearrangement of Arylsulfonium Species2021

    • Author(s)
      Yanagi Tomoyuki、Yorimitsu Hideki
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 53 Pages: 13450-13456

    • DOI

      10.1002/chem.202101735

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N-Ts Bond in a Different Light2021

    • Author(s)
      Ozaki Tomoya、Yorimitsu Hideki、Perry Gregory J. P.
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 62 Pages: 15387-15391

    • DOI

      10.1002/chem.202102748

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reductive Cleavage of Propargylic Ethers with Alkali Metal: Application to the Synthesis of Allenylboronates2021

    • Author(s)
      Koyama Shunsuke、Takahashi Fumiya、Saito Hayate、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 21 Pages: 8590-8594

    • DOI

      10.1021/acs.orglett.1c03316

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of 5H‐Dibenzo[c,e]azepine Framework from Dibenzothiophene Dioxides and N‐Benzylimines through SNAr Reactions2021

    • Author(s)
      Furukawa Tomoki、Yanagi Tomoyuki、Kaga Atsushi、Saito Hayate、Yorimitsu Hideki
    • Journal Title

      Helvetica Chimica Acta

      Volume: 104 Issue: 12

    • DOI

      10.1002/hlca.202100195

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Transformations of Sulfonium Salts via C‐S Bond Activation2021

    • Author(s)
      Yorimitsu Hideki
    • Journal Title

      The Chemical Record

      Volume: 21 Issue: 12 Pages: 3356-3369

    • DOI

      10.1002/tcr.202000172

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation2021

    • Author(s)
      Kaga Atsushi、Iida Hirokazu、Tsuchiya Shun、Saito Hayate、Nakano Koji、Yorimitsu Hideki
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 14 Pages: 4567-4572

    • DOI

      10.1002/chem.202005223

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Asymmetric Systematic Synthesis, Structures, and (Chir)optical Properties of a Series of Dihetero[8]helicenes2021

    • Author(s)
      Tomoyuki Yanagi, Takayuki Tanaka and Hideki Yorimitsu
    • Journal Title

      Chemical Science

      Volume: 12 Issue: 8 Pages: 2784-2793

    • DOI

      10.1039/d1sc00044f

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] On the Order of Addition of Sodium Dispersion in Reductive Diborations of Stilbene and 1,2-Diphenylcyclopropane2021

    • Author(s)
      Yorimitsu Hideki、Wang Shuo、Kaga Atsushi
    • Journal Title

      HETEROCYCLES

      Volume: 103 Issue: 2 Pages: 1057-1057

    • DOI

      10.3987/com-20-s(k)59

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Silylation of Aryl Chlorides with Bulky Dialkoxydisilanes2020

    • Author(s)
      Shimokawa Jun、Yorimitsu Hideki、Fukui Keitaro、Saito Hayate
    • Journal Title

      Synlett

      Volume: - Issue: 13 Pages: 1328-1332

    • DOI

      10.1055/s-0039-1690877

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium‐Catalyzed peri‐Selective C-H Fluoroalkoxylation of Aryl Sulfoxides2020

    • Author(s)
      Sato Tomohiko、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      ChemCatChem

      Volume: 12 Issue: 13 Pages: 3467-3471

    • DOI

      10.1002/cctc.202000485

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sodium-Metal-Promoted Reductive 1,2-syn-Diboration of Alkynes with Reduction-Resistant Trimethoxyborane2020

    • Author(s)
      Ito Shiori、Fukazawa Mizuki、Takahashi Fumiya、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 93 Issue: 10 Pages: 1171-1179

    • DOI

      10.1246/bcsj.20200110

    • NAID

      130007926134

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Copper-Catalyzed Electrophilic Amination of Alkoxyarylsilanes2020

    • Author(s)
      Zhang Qian、Hitoshio Kenshiro、Saito Hayate、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2020 Issue: 26 Pages: 4018-4021

    • DOI

      10.1002/ejoc.202000562

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Palladium‐Catalyzed C-H Iodination of Arenes by Means of Sulfinyl Directing Groups2020

    • Author(s)
      Saito Hayate、Yamamoto Keita、Sumiya Yosuke、Liu Ling‐Jun、Nogi Keisuke、Maeda Satoshi、Yorimitsu Hideki
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 15 Issue: 16 Pages: 2442-2446

    • DOI

      10.1002/asia.202000591

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Regioselective Difunctionalization of 2,6-Difluorophenols Triggered by Sigmatropic Dearomatization2020

    • Author(s)
      Okamoto Koichi、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 14 Pages: 5540-5544

    • DOI

      10.1021/acs.orglett.0c01904

    • NAID

      120006895436

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Route to Indoles via Modified Fischer Indole Intermediates from Sulfonanilides and Ketene Dithioacetal Monoxides2020

    • Author(s)
      Jun Kinoshita, Alexandre Baralle, Akira Yoshida, Tomoyuki Yanagi, Keisuke Nogi, Hideki Yorimitsu
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 9 Issue: 10 Pages: 1655-1659

    • DOI

      10.1002/ajoc.202000397

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust2020

    • Author(s)
      Kodai Yamada, Tomoyuki Yanagi, Hideki Yorimitsu
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 24 Pages: 9712-9718

    • DOI

      10.1021/acs.orglett.0c03782

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal2020

    • Author(s)
      Yorimitsu Hideki、Wang Shuo、Kaga Atsushi
    • Journal Title

      Synlett

      Volume: 32 Issue: 02 Pages: 219-223

    • DOI

      10.1055/s-0040-1706538

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Metal-Free Synthesis of Biaryls from Aryl Sulfoxides and Sulfonanilides via Sigmatropic Rearrangement2020

    • Author(s)
      Akira Yoshida, Koichi Okamoto, Tomoyuki Yanagi, Keisuke Nogi, Hideki Yorimitsu
    • Journal Title

      Tetrahedron

      Volume: 76 Issue: 51 Pages: 131232-131232

    • DOI

      10.1016/j.tet.2020.131232

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic C?H Arylation of Tetrathiafulvalenes for the Synthesis of Functional Materials2020

    • Author(s)
      Yorimitsu Hideki、Yoshimura Aya、Misaki Yohji
    • Journal Title

      Synthesis

      Volume: 52 Issue: 22 Pages: 3326-3336

    • DOI

      10.1055/s-0040-1707256

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbon-Carbon Bond Cleavage at Allylic Positions: Retro-allylation and Deallylation2020

    • Author(s)
      Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Chemical Reviews

      Volume: 121 Issue: 1 Pages: 345-364

    • DOI

      10.1021/acs.chemrev.0c00157

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electron injection for aromatic metamorphosis of indole2020

    • Author(s)
      Yorimitsu Hideki
    • Journal Title

      Journal of the Chinese Chemical Society

      Volume: 68 Issue: 4 Pages: 536-540

    • DOI

      10.1002/jccs.202000369

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ni-Catalyzed Carboxylation of C(sp2)?S Bonds with CO2: Evidence for the Multifaceted Role of Zn2020

    • Author(s)
      Yanagi Tomoyuki、Somerville Rosie J.、Nogi Keisuke、Martin Ruben、Yorimitsu Hideki
    • Journal Title

      ACS Catalysis

      Volume: 10 Issue: 3 Pages: 2117-2123

    • DOI

      10.1021/acscatal.9b05141

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Tf2O-mediated Reaction of Alkenyl Sulfoxides with Unprotected Anilines in Flow Microreactors2020

    • Author(s)
      Baralle Alexandre、Inukai Tomoaki、Yanagi Tomoyuki、Nogi Keisuke、Osuka Atsuhiro、Nagaki Aiichiro、Yoshida Jun-ichi、Yorimitsu Hideki
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 2 Pages: 160-163

    • DOI

      10.1246/cl.190831

    • NAID

      130007795212

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles2020

    • Author(s)
      Fukazawa Mizuki、Takahashi Fumiya、Nogi Keisuke、Sasamori Takahiro、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 6 Pages: 2303-2307

    • DOI

      10.1021/acs.orglett.0c00490

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] B2cat2-Mediated Reduction of Sulfoxides to Sulfides2020

    • Author(s)
      Takahashi Fumiya、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2020 Issue: 20 Pages: 3009-3012

    • DOI

      10.1002/ejoc.202000222

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] C-F Arylation of Polyfluorophenols by Means of Sigmatropic Dearomatization/Defluorination Sequence2020

    • Author(s)
      Okamoto Koichi、Nogi Keisuke、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      Chemistry - A European Journal

      Volume: 26 Issue: 25 Pages: 5615-5618

    • DOI

      10.1002/chem.202001158

    • NAID

      120006895437

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Carbonylation and Carboxylation of Organosulfur Compounds via C-S Cleavage2020

    • Author(s)
      Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 15 Issue: 4 Pages: 441-449

    • DOI

      10.1002/asia.201901644

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Diborative Reduction of Alkynes to 1,2-Diboryl-1,2-Dimetalloalkanes: Its Application for the Synthesis of Diverse 1,2-Bis(boronate)s2019

    • Author(s)
      Takahashi Fumiya、Nogi Keisuke、Sasamori Takahiro、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 12 Pages: 4739-4744

    • DOI

      10.1021/acs.orglett.9b01622

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Twofold Silylmetalation of Alkynes2019

    • Author(s)
      Yamagishi Hiroki、Shimokawa Jun、Yorimitsu Hideki
    • Journal Title

      Synlett

      Volume: 30 Issue: 13 Pages: 1551-1554

    • DOI

      10.1055/s-0037-1611869

    • NAID

      120006715508

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Arylthiolation of Alkynes Enabled by Surmounting Competitive Dimerization of Alkynes2019

    • Author(s)
      Uno Daisuke、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 20 Pages: 8295-8299

    • DOI

      10.1021/acs.orglett.9b03056

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of N-Alkyl and N-H Carbazoles via SNAr‐based Aminations of Dibenzothiophene dioxides2019

    • Author(s)
      Kaga Atsushi、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 65 Pages: 14780-14784

    • DOI

      10.1002/chem.201903916

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cross-Coupling of Aryl Trifluoromethyl Sulfones with Arylboronates by Cooperative Palladium/Rhodium Catalysis2019

    • Author(s)
      Fukuda Jun-ichi、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 22 Pages: 8987-8991

    • DOI

      10.1021/acs.orglett.9b03393

    • NAID

      120006800717

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Biaryls from Aryl Sulfoxides and Anilines by Means of a Sigmatropic Rearrangement2019

    • Author(s)
      Yanagi Tomoyuki、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Chemistry A European Journal

      Volume: 26 Issue: 4 Pages: 783-787

    • DOI

      10.1002/chem.201903570

    • NAID

      120006800745

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring-expanding and Ring-opening Transformations of Benzofurans and Indoles with Introducing Heteroatoms2019

    • Author(s)
      Saito Hayate、Yorimitsu Hideki
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 9 Pages: 1019-1028

    • DOI

      10.1246/cl.190393

    • NAID

      130007703022

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] Reductive Dimetalation of Alkynes2024

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      2024 International Organic and Bioorganic Symposium
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reductive Borylmetallation of Alkynes Enabled by Flow Microreactors2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      GRAMS-Korea Symposium on Microchemistry 2023
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Aromatic Metamorphosis2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      KAUST Research Conference: Advances in Sustainable Catalysis
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Aromatic Metamorphosis of Thiophenes2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      Joint Workshop on the Organic Chemistry of Sulfur
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reductive Metalation of Unsaturated Bonds by Taming Radical Anions2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      10th Pacific Symposium on Radical Chemistry
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 芳香環の骨格編集:芳香環メタモルフォシス2023

    • Author(s)
      依光英樹
    • Organizer
      近畿化学協会合成部会 令和5年度第1回フォーラム
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Aromatic Metamorphosis2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      22nd Conference of the Doctoral School
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reductive Metalation of Unsaturated Bonds by Taming Radical Anions2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      23rd International Conference on Organic Synthesis
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reductive Dimetalation of Unsaturated Bonds2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      Catalysis & Fine Chemicals-2023
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Aromatic Metamorphosis2023

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      Indo-French Seminar on Catalysis for Sustainability
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] スルホニウム中間体を活用する有機合成2022

    • Author(s)
      依光英樹
    • Organizer
      第18回フッ素相模セミナー
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Aromatic Metamorphosis of Thiophenes2022

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      29th International Symposium on the Organic Chemistry of Sulfur
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reductive Metalation of Unsaturated Bonds in the Presence of Electrophiles2022

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      5th Conference on Advanced Organic Synthesis
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reductive anti-Dimagnesiatio and Dialumination of Alkynes2022

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      15th International Symposium on Organic Reactions
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 不飽和結合への電子注入制御に基づくカルボアニオンの発生と利用2022

    • Author(s)
      依光英樹
    • Organizer
      フローマイクロ合成研究会第96回研究会
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Dimetallation of Alkynes through Electron Injection2022

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      International Symposium on Innovative Reactions through Controlling Electrons
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 金属ナトリウムを用いたシクロプロパンの開環シクロプロパンカルボキシアミドの開環二官能基化2022

    • Author(s)
      王 爍、加賀 敦志、黒木 尭、依光 英樹
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 単体アルカリ金属を用いたアリールシリルエーテルの炭素-酸素結合の還元的切断2022

    • Author(s)
      淺井大揮、高橋郁也、齊藤颯、依光英樹
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 金属ナトリウムを用いた1,2-ジボリル-1,2-ジアリールエタンの還元的炭素-炭素結合切断によるボリルベンジルアニオンの発生2022

    • Author(s)
      深澤瑞喜、高橋郁也、依光英樹
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 炭酸ビニルの還元的ジボリル化を経るビニルボロン酸エステル合成2022

    • Author(s)
      児山駿介、高橋郁也、齊藤颯、依光英樹
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Sulfonyl Pyrroles: Synthetic Linchpins for Late-Stage Functionalization of Primary Sulfonamides2022

    • Author(s)
      Tomoya Ozaki、Hideki Yorimitsu、Gregory J. P. Perry
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 不飽和化合物への電子注入制御に基づくカルボアニオンの発生と利用2021

    • Author(s)
      依光英樹
    • Organizer
      第19回化学系若手研究者セミナー(日本薬学会東北支部)
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Aromatic Metamorphosis of Thiophenes2021

    • Author(s)
      依光英樹
    • Organizer
      Pacifichem 2021 Sulfur Rush
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 金属ナトリウムによる還元を用いた多環芳香族炭化水素のボリル化2021

    • Author(s)
      深澤瑞喜、高橋郁也、依光英樹
    • Organizer
      第48回有機典型元素化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] プロパルギルエーテルの還元的CO結合切断を用いたアレニルボロン酸エステルの合成2021

    • Author(s)
      児山駿介、高橋郁也、齊藤颯、依光英樹
    • Organizer
      第48回有機典型元素化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ナトリウム金属を用いたシクロプロパンの開環1,3-二官能基化反応2021

    • Author(s)
      王爍・加賀敦志・依光英樹
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] プロパルギルエーテルの還元を用いた四置換アレニルボロン酸エステル合成2021

    • Author(s)
      児山 駿介、高橋 郁也、依光 英樹
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 金属ナトリウムによる還元を用いたベンゾトリフルオリド類の脱フッ素ジボリル化2021

    • Author(s)
      伊藤 詩織、高橋 郁也、依光 英樹
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 金属ナトリウムによる還元を用いた多環芳香族炭化水素のボリル化2021

    • Author(s)
      深澤 瑞喜、高橋 郁也、依光 英樹
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 金属リチウムを用いたN―アリールピロールの還元的な炭素―窒素結合切断2021

    • Author(s)
      尾崎 友哉、加賀 敦志、依光 英樹
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 金属ナトリウムによる還元を用いたアルキンの1,2-ジマグネシウム化および1,2-ジアルミニウム化2021

    • Author(s)
      高橋 郁也、依光 英樹
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Electron Injection into Unsaturated Molecules in the Presence of Electrophiles2020

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      International Symposium on Advanced Science and Technology
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 忍法 脱芳香族化2020

    • Author(s)
      依光英樹
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 電子注入に基づく不飽和分子の活性化と有機合成への利用2020

    • Author(s)
      依光英樹
    • Organizer
      2020プロセス化学会ウィンターシンポジウム
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] アルカリ金属を用いたシクロプロパンの開環1,3-二官能基化反応2020

    • Author(s)
      王爍・加賀敦志・依光英樹
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 金属ナトリウムとトリメトキシボランを用いたアルキンの1,2-ジボリル化2020

    • Author(s)
      伊藤詩織・深澤瑞喜・高橋郁也・依光英樹
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 金属ナトリウムを用いたアルケンの還元的二重官能基化2020

    • Author(s)
      深澤瑞喜・高橋郁也・依光英樹
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ニッケル触媒によるアリールスルホニウム塩の還元的亜鉛化2020

    • Author(s)
      山田航大・柳智征・依光英樹
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] チオフェン類の脱硫的ジリチオ化に基づく芳香環メタモルフォシス2020

    • Author(s)
      加賀敦志・依光英樹
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 不飽和結合への電子注入に基づく高度官能基化法の創出2020

    • Author(s)
      依光英樹
    • Organizer
      第四回有機化学シンポジウム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 金属ナトリウムを用いたアルケンの還元的二重官能基化2020

    • Author(s)
      深澤瑞喜・高橋郁也・野木馨介・依光英樹
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 金属ナトリウムとトリメトキシボランを用いたアルキンの還元的ジボリル化2020

    • Author(s)
      伊藤詩織・深澤瑞喜・高橋郁也・野木馨介・依光英樹
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 新反応を追求する化学者の計算化学との付き合い方2019

    • Author(s)
      依光英樹
    • Organizer
      近畿化学協会コンピュータ化学部会第105回例会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 芳香環メタモルフォシス2019

    • Author(s)
      依光英樹
    • Organizer
      第6回次世代の有機化学・広島シンポジウム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Aromatic Metamorphosis: Breaking Aromaticity to Construct New Cyclic Systems2019

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      The 1st KU-UNIST Joint Symposium on Chemistry and Materials Science
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Aromatic Metamorphosis of Benzofurans2019

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      International Symposium of Precisely Designed Catalysts with Customized Scaffolding
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Aromatic Metamorphosis for the Synthesis of Azaarenes2019

    • Author(s)
      Hideki Yorimitsu
    • Organizer
      The 2nd Sino-Japanese Symposium on Catalysis for Precision Synthesis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 金属ナトリウムとトリアルコキシボランを用いたアルケンの 1,2-ジボリル化2019

    • Author(s)
      深澤 瑞喜・ 高橋 郁也・野木 馨介・依光 英樹
    • Organizer
      第66回有機金属化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 単体アルカリ金属を用いたアルキンのジボリル化還元による1,2-ジボリル-1,2-ジメタロアルカンの発生2019

    • Author(s)
      野木 馨介・高橋 郁也・笹森 貴裕・依光 英樹
    • Organizer
      第66回有機金属化学討論会
    • Related Report
      2019 Annual Research Report
  • [Remarks] 研究室HP

    • URL

      http://kuchem.kyoto-u.ac.jp/orgchem/

    • Related Report
      2022 Annual Research Report
  • [Remarks] 「驚きの有機化学反応を創り育てる」 依光英樹, 京都大学理学研究科・理学部研究紹介インタビュー

    • URL

      http://www.sci.kyoto-u.ac.jp/ja/research/activities-ch/1910-hidekiyorimitsu.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] 化学専攻 依光英樹教授が日本学術振興会賞を受賞

    • URL

      http://www.sci.kyoto-u.ac.jp/ja/news/detail_1557.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] 化学専攻 依光英樹教授が日本学士院学術奨励賞を受賞

    • URL

      http://www.sci.kyoto-u.ac.jp/ja/news/detail_1575.htmlhttp://kuchem.kyoto-u.ac.jp/orgchem/

    • Related Report
      2019 Annual Research Report
  • [Remarks] 依光英樹 理学研究科教授が第16回(令和元年度)日本学士院学術奨励賞を受賞

    • URL

      https://www.kyoto-u.ac.jp/ja/news/2020-01-23-0

    • Related Report
      2019 Annual Research Report

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Published: 2019-04-18   Modified: 2025-01-30  

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