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Development bond exchange reaction and optimization reaction conditions using Machine Learning

Planned Research

Project AreaDigitalization-driven Transformative Organic Synthesis (Digi-TOS)
Project/Area Number 21H05213
Research Category

Grant-in-Aid for Transformative Research Areas (A)

Allocation TypeSingle-year Grants
Review Section Transformative Research Areas, Section (II)
Research InstitutionWaseda University

Principal Investigator

山口 潤一郎  早稲田大学, 理工学術院, 教授 (00529026)

Project Period (FY) 2021-09-10 – 2026-03-31
Project Status Granted (Fiscal Year 2024)
Budget Amount *help
¥38,870,000 (Direct Cost: ¥29,900,000、Indirect Cost: ¥8,970,000)
Fiscal Year 2025: ¥7,410,000 (Direct Cost: ¥5,700,000、Indirect Cost: ¥1,710,000)
Fiscal Year 2024: ¥7,020,000 (Direct Cost: ¥5,400,000、Indirect Cost: ¥1,620,000)
Fiscal Year 2023: ¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
Fiscal Year 2022: ¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
Fiscal Year 2021: ¥9,880,000 (Direct Cost: ¥7,600,000、Indirect Cost: ¥2,280,000)
Keywords分子編集 / ヘテロ環 / 芳香族ケトン / 結合交換 / エステル / ニッケル / パラジウム / 芳香族ニトロ化合物 / 結合交換反応 / 金属触媒 / 芳香族化合物 / 官能基 / 機械学習 / 芳香環交換反応 / クロスカップリング / ニトリル / スルフィド / アリール交換
Outline of Research at the Start

本研究は、申請者らが見いだした異種結合交換反応(アリール交換反応)に適用可能な芳香環の拡大、さらに多種な結合交換が可能な触媒開発に着手する。具体的には、エステル・ニトロ基・ケトン・エーテル・ニトリルなどの不活性結合を同時に活性化可能な触媒を用いた結合交換反応により安価で入手容易な化合物から高付加価値の化合物を合成する。さらに、最も高反応性官能基であるハロゲンを残したまま不活性結合を活性化し得る反応系の探索に挑戦する。触媒設計と適用できる化合物群の選定は結合解離エネルギーと触媒構造の適切なパラメータ化を用いて機械学習によって得られた知見を最短の最適化法として駆使する。

Outline of Annual Research Achievements

本研究は、申請者らが見いだした異種結合交換反応(アリール交換反応)に適用可能な芳香環の拡大、さらに多種な結合交換が可能な触媒開発に着手する。。具体的には、エステル・ニトロ基・ケトン・エーテル・ニトリルなどの不活性結合を同時に活性化可能な触媒を用いた結合交換反応により安価で入手容易な化合物から高付加価値の化合物を合成する。
これらの反応を進行させるためには、2種類の不活性結合の活性化が必要となる。それらを探索中に、芳香族ニトロ化合物のニトロ化反応、多様な芳香族化合物のチオメチル化反応を見出すことができた。関連研究として、芳香族ケトンの脱アシル型カップリング反応(結合交換反応を含む)、脱酸素型カップリング反応を開発した。その他、脱芳香族的官能基化反応として、アザアレーンの開環型ジフルオロ化反応や分子内環化/脱芳香族化反応(すぐに芳香環化する)を見出した。

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

結合交換反応に関しては、今年度多くの進展はなかったが、その他の関連反応探索が順調であり、機械学習に関しても研究をすすめているため、おおむね順調に進呈しているとした。

Strategy for Future Research Activity

引き続き結合交換反応を探索する。現在見出している関連した反応に関しても論文としてまとめ公開する

Report

(3 results)
  • 2023 Annual Research Report
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (34 results)

All 2023 2022 2021

All Journal Article (25 results) (of which Peer Reviewed: 22 results,  Open Access: 7 results) Presentation (9 results) (of which Int'l Joint Research: 2 results,  Invited: 7 results)

  • [Journal Article] Ring‐opening Fluorination of Carbo/Heterocycles and Aromatics: Construction of Complex and Diverse Fluorine‐containing Molecules2023

    • Author(s)
      Komatsuda Masaaki、Yamaguchi Junichiro
    • Journal Title

      The Chemical Record

      Volume: - Issue: 9

    • DOI

      10.1002/tcr.202200281

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Activation of Alkyl Chlorides Enabled by Zirconocene and Photoredox Catalysis2023

    • Author(s)
      Okita Toshimasa、Aida Kazuhiro、Tanaka Keisuke、Ota Eisuke、Yamaguchi Junichiro
    • Journal Title

      Precis. Chem.

      Volume: 1 Pages: 112-118

    • DOI

      10.26434/chemrxiv-2022-5n811

    • Related Report
      2023 Annual Research Report
  • [Journal Article] Pd-Catalyzed Denitriative Intramolecular Mizoroki?Heck Reaction2023

    • Author(s)
      Asahara Kitty K.、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      Chemistry Letters

      Volume: - Issue: 4 Pages: 299-302

    • DOI

      10.1246/cl.230056

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chloroacetyl boronate <i>N</i>-tosylhydrazone as a versatile synthetic building block2023

    • Author(s)
      Miyazaki Ryuya、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      Chemical Communications

      Volume: 59 Issue: 48 Pages: 7419-7422

    • DOI

      10.1039/d3cc02086j

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Repurposing carboxylic acids and alcohols/amines to create α-hydroxy/amino ketones2023

    • Author(s)
      Ishihara Yoshihiro、Yamaguchi Junichiro
    • Journal Title

      Chem

      Volume: 9 Issue: 7 Pages: 1630-1632

    • DOI

      10.1016/j.chempr.2023.06.004

    • Related Report
      2023 Annual Research Report
  • [Journal Article] Concise synthesis of (±)-fortuneicyclidins and (±)-cephalotine B enabled by Pd-catalyzed dearomative spirocyclization2023

    • Author(s)
      Uwabe Yota、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      Chem. E. J.

      Volume: 29

    • DOI

      10.26434/chemrxiv-2023-jx26c-v2

    • Related Report
      2023 Annual Research Report
  • [Journal Article] Catalytic reductive ring opening of epoxides enabled by zirconocene and photoredox catalysis2022

    • Author(s)
      Aida Kazuhiro、Hirao Marina、Funabashi Aiko、Sugimura Natsuhiko、Ota Eisuke、Yamaguchi Junichiro
    • Journal Title

      Chem

      Volume: 8 Issue: 6 Pages: 1762-1774

    • DOI

      10.1016/j.chempr.2022.04.010

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Decarbonylative Reductive Coupling of Aromatic Esters by Nickel and Palladium Catalyst2022

    • Author(s)
      Peng Yunfei、Isshiki Ryota、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      Chemistry Letters

      Volume: 51 Issue: 7 Pages: 749-753

    • DOI

      10.1246/cl.220214

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions2022

    • Author(s)
      Kubo Masayuki、Inayama Naomi、Ota Eisuke、Yamaguchi Junichiro
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 21 Pages: 3855-3860

    • DOI

      10.1021/acs.orglett.2c01432

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-Catalyzed 1,4-Carboamination of Bicyclic Bromoarenes with Diazo Compounds and Amines2022

    • Author(s)
      Wu Qikun、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 23 Pages: 4129-4134

    • DOI

      10.1021/acs.orglett.2c01233

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical biology to dissect molecular mechanisms underlying plant circadian clocks2022

    • Author(s)
      Nakamichi Norihito、Yamaguchi Junichiro、Sato Ayato、Fujimoto Kazuhiro J.、Ota Eisuke
    • Journal Title

      New Phytologist

      Volume: 235 Issue: 4 Pages: 1336-1343

    • DOI

      10.1111/nph.18298

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Identification of α-Synuclein Proaggregator: Rapid Synthesis and Streamlining RT-QuIC Assays in Parkinson’s Disease2022

    • Author(s)
      Takada Fumito、Kasahara Takahito、Otake Kentaro、Maru Takamitsu、Miwa Masanori、Muto Kei、Sasaki Minoru、Hirozane Yoshihiko、Yoshikawa Masato、Yamaguchi Junichiro
    • Journal Title

      ACS Medicinal Chemistry Letters

      Volume: 13 Issue: 9 Pages: 1421-1426

    • DOI

      10.1021/acsmedchemlett.2c00138

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Unified synthesis of multiply arylated alkanes by catalytic deoxygenative transformation of diarylketones2022

    • Author(s)
      Kurosawa Miki B.、Kato Kenta、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      Chemical Science

      Volume: 13 Issue: 36 Pages: 10743-10751

    • DOI

      10.1039/d2sc03720c

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and Properties of Pyridine-Fused Triazolylidene?Palladium: Catalyst for Cross-Coupling Using Chloroarenes and Nitroarenes2022

    • Author(s)
      Iizumi Keiichiro、Nakayama Keito P.、Kato Kenta、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 17 Pages: 11909-11918

    • DOI

      10.1021/acs.joc.2c01562

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure?Function Study of a Novel Inhibitor of Cyclin-Dependent Kinase C in Arabidopsis2022

    • Author(s)
      Saito Ami N、Maeda Akari E、Takahara Tomoaki T、Matsuo Hiromi、Nishina Michiya、Ono Azusa、Shiratake Katsuhiro、Notaguchi Michitaka、Yanai Takeshi、Kinoshita Toshinori、Ota Eisuke、Fujimoto Kazuhiro J、Yamaguchi Junichiro、Nakamichi Norihito
    • Journal Title

      Plant and Cell Physiology

      Volume: 63 Issue: 11 Pages: 1720-1728

    • DOI

      10.1093/pcp/pcac127

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Aryl Dance Reaction of Arylbenzoheteroles2022

    • Author(s)
      Nakahara Hikaru、Yamaguchi Junichiro
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 43 Pages: 8083-8087

    • DOI

      10.1021/acs.orglett.2c03442

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring-opening fluorination of bicyclic azaarenes2022

    • Author(s)
      Komatsuda Masaaki、Suto Ayane、Kondo Hiroki、Takada Hiroyuki、Kato Kenta、Saito Bunnai、Yamaguchi Junichiro
    • Journal Title

      Chemical Science

      Volume: 13 Issue: 3 Pages: 665-670

    • DOI

      10.1039/d1sc06273e

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy2022

    • Author(s)
      Nie Yu-Han、Komatsuda Masaaki、Yang Ping、Zheng Chao、Yamaguchi Junichiro、You Shu-Li
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 7 Pages: 1481-1485

    • DOI

      10.1021/acs.orglett.2c00129

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal Syntheses of Dictyodendrins B, C, and E by a Multi-substituted Indole Synthesis2022

    • Author(s)
      Kabuki Akira、Yamaguchi Junichiro
    • Journal Title

      Synthesis

      Volume: - Issue: 22 Pages: 4963-4970

    • DOI

      10.1055/a-1786-9881

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring-Opening Fluorination of Isoxazoles2022

    • Author(s)
      Komatsuda Masaaki、Ohki Hugo、Kondo Hiroki、Suto Ayane、Yamaguchi Junichiro
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 17 Pages: 3270-3274

    • DOI

      10.1021/acs.orglett.2c01149

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorination -A Decade of Progress (2010-2020)2021

    • Author(s)
      Suto Ayane、Yamaguchi Junichiro
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 79 Issue: 10 Pages: 910-967

    • DOI

      10.5059/yukigoseikyokaishi.79.910

    • NAID

      130008102165

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2021-10-01
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Pd-Catalyzed Denitrative Couplings2021

    • Author(s)
      淺原光太郎, 柏原美勇斗, 武藤慶, 中尾佳亮, 山口潤一郎
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 79 Issue: 1 Pages: 11-21

    • DOI

      10.5059/yukigoseikyokaishi.79.11

    • NAID

      130007966738

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2021-01-01
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst2021

    • Author(s)
      Yamaguchi Junichiro、Iizumi Keiichiro、Kurosawa Miki B.、Isshiki Ryota、Muto Kei
    • Journal Title

      Synlett

      Volume: 32 Issue: 15 Pages: 1555-1559

    • DOI

      10.1055/s-0040-1705943

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction2021

    • Author(s)
      Isshiki Ryota、Kurosawa Miki B.、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 27 Pages: 10333-10340

    • DOI

      10.1021/jacs.1c04215

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Convergent Azaspirocyclization of Bromoarenes with <i>N</i>-Tosylhydrazones by a Palladium Catalyst2021

    • Author(s)
      Yanagimoto Aika、Uwabe Yota、Wu Qikun、Muto Kei、Yamaguchi Junichiro
    • Journal Title

      ACS Catalysis

      Volume: 11 Issue: 16 Pages: 10429-10435

    • DOI

      10.1021/acscatal.1c02627

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Presentation] 開環型フッ素化反応と脱フッ素化反応2023

    • Author(s)
      山口潤一郎
    • Organizer
      京都大学講演会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] Unconventional Recipes for Aromatic Carbonyls Transformations2023

    • Author(s)
      Junichiro Yamaguchi
    • Organizer
      北京大学講演会
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Unconventional Recipes for Aromatic Carbonyls Transformations2023

    • Author(s)
      Junichiro Yamaguchi
    • Organizer
      西安交通大学講演会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 有機合成化学の新潮流をつくる2023

    • Author(s)
      山口潤一郎
    • Organizer
      先進研究講演会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] 開環型フッ素化反応と脱フッ素化反応2023

    • Author(s)
      山口潤一郎
    • Organizer
      大阪大学講演会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] Breaking C-F Bonds: Novel Strategies Using Polar and Radical Reactions2023

    • Author(s)
      Junichiro Yamaguchi
    • Organizer
      7th Gratama Workshop 2023
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 開環型フッ素化反応と脱フッ素化反応2023

    • Author(s)
      山口潤一郎
    • Organizer
      日本フッ素化学会第10回産学連携部会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] 応用化学科の現状と分子レベルのものづくり研究2023

    • Author(s)
      山口潤一郎
    • Organizer
      早稲田応用化学会中部支部
    • Related Report
      2023 Annual Research Report
  • [Presentation] 高難度有機反応の開発と医農薬関連企業との共同研究2021

    • Author(s)
      山口潤一郎
    • Organizer
      第31回万有福岡シンポジウム 有機合成化学の変革~未踏の森に飛び込もう~
    • Related Report
      2021 Annual Research Report
    • Invited

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Published: 2021-10-22   Modified: 2025-04-17  

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