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Development of Catalytic Aminoboration of Alkenes

Research Project

Project/Area Number 25620084
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

Hirano Koji  大阪大学, 工学(系)研究科(研究院), 准教授 (70532696)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsアミノホウ素化 / ヒドロアミノ化 / 求電子的アミノ化 / アミン / アルケン / 有機ホウ素化合物 / 触媒的不斉合成 / 位置選択性 / アミノ化 / 銅触媒 / αーアミノホウ酸 / アルキルアミン / 光学活性アミン
Outline of Final Research Achievements

We have developed copper-catalyzed regio-and stereoselective aminoborations of alkenes by using an electrophilic amination as a key step. Under optimal conditions, electronically activated styrenes as well as strained methylenecyclopropanes and bicyclic alkenes could be employed. Additionally, we successfully found an efficient Cu-based catalyst system for the challenging unactivated terminal alkenes, which are know to be feedstock materials. The obtained aminoboration products can be useful intermediates in organic synthesis because the resulting boron functionality can be a versatile synthetic handle for further transformation. Additionally, related regio- and enantioselective hydroamination catalysis was also developed.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (38 results)

All 2016 2015 2014 2013 Other

All Journal Article (26 results) (of which Peer Reviewed: 26 results,  Acknowledgement Compliant: 13 results,  Open Access: 1 results) Presentation (9 results) (of which Int'l Joint Research: 2 results,  Invited: 7 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Palladium-Catalyzed Asymmetric Benzylic Alkylation of Active Methylene Compounds with α-Naphthylbenzyl Carbonates and Pivalates2016

    • Author(s)
      Sho Tabuchi, Koji Hirano, Masahiro Miura
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 印刷中 Issue: 24 Pages: 6973-6977

    • DOI

      10.1002/anie.201602075

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ligand-Controlled Regiodivergent Cu-Catalyzed Aminoboration of Unactivated Terminal Alkenes2015

    • Author(s)
      Ryosuke Sake, Koji Hirano, Masahiro Miura
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 20 Pages: 6460-6463

    • DOI

      10.1021/jacs.5b02775

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Mediated Oxidative Coupling of Benzamides with Maleimides via Directed C-H Cleavage2015

    • Author(s)
      Wataru Miura, Koji Hirano, Masahiro Miura
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 16 Pages: 4034-4037

    • DOI

      10.1021/acs.orglett.5b01940

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Formal [4 + 1] Cycloaddition of Benzamides and Isonitriles via Directed C-H Cleavage2015

    • Author(s)
      Kazutaka Takamatsu, Koji Hirano Masahiro Miura
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 16 Pages: 4066-4069

    • DOI

      10.1021/acs.orglett.5b01986

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereospecific Pd-Catalyzed Intermolecular C(sp3)-C(sp) Cross-Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base-Free Conditions2015

    • Author(s)
      Sho Tabuchi, Koji Hirano, Masahiro Miura
    • Journal Title

      Chemistry-A European Journal

      Volume: 21 Issue: 47 Pages: 16823-16827

    • DOI

      10.1002/chem.201503647

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Synthesis of α-Aminoboronic Acid Derivatives by Copper-Catalyzed Enantioselective Hydroamination2015

    • Author(s)
      Daiki Nishikawa, Koji Hirano, Masahiro Miura
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 50 Pages: 15620-15623

    • DOI

      10.1021/jacs.5b09773

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Stereoselective Aminoboration of Bicyclic Alkenes2015

    • Author(s)
      Ryosuke Sakae, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 54 Issue: 2 Pages: 613-617

    • DOI

      10.1002/anie.201409104

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Mediated Formally Dehydrative Biaryl Coupling of Azine N-Oxides and Oxazoles2015

    • Author(s)
      Riko Odani, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 4 Pages: 2384-2391

    • DOI

      10.1021/acs.joc.5b00037

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Indolines by Copper-Mediated Intramolecular Aromatic C-H Amination2015

    • Author(s)
      Kazutaka Takamatsu, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 6 Pages: 3242-3249

    • DOI

      10.1021/acs.joc.5b00307

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Recent Advances in Copper-mediated Direct Biaryl Coupling2015

    • Author(s)
      Koji Hirano, Masahiro Miura
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 7 Pages: 868-873

    • DOI

      10.1246/cl.150354

    • NAID

      130005085180

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C-H/N-H Coupling2014

    • Author(s)
      Kazutaka Takamatsu, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 11 Pages: 2892-2895

    • DOI

      10.1021/ol501037j

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Triarylmethanes by Palladium-Catalyzed C-H/C-O Coupling of Oxazoles and Diarylmethanol Derivatives2014

    • Author(s)
      Sho Tabuchi, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 79 Issue: 12 Pages: 5401-5411

    • DOI

      10.1021/jo5010636

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Mediated C6-Selective Dehydrogenative Heteroarylation of 2-Pyridones with 1,3-Azoles2014

    • Author(s)
      Riko Odani, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 53 Issue: 40 Pages: 10784-10788

    • DOI

      10.1002/anie.201406228

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Mediated Regioselective Homocoupling of Thiophenes and Indoles via Directed C-H Cleavage2014

    • Author(s)
      Riko Odani, Mayuko Nishino, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Heterocycles

      Volume: 88 Issue: 1 Pages: 595-602

    • DOI

      10.3987/com-13-s(s)4

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Manganese-Mediated C3-Selective Direct Alkylation and Arylation of 2-Pyridones with Diethyl Malonates and Arylboronic Acids2014

    • Author(s)
      Akihiro Nakatani, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 79 Issue: 3 Pages: 1377-1385

    • DOI

      10.1021/jo4027885

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Highly Stereoselective Synthesis of (Borylmethyl)cyclopropylamines by Copper-Catalyzed Aminoboration of Methylenecyclopropanes2014

    • Author(s)
      Ryosuke Sakae
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 4 Pages: 1228-1231

    • DOI

      10.1021/ol5001507

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-catalyzed aminoboration and hydroamination of alkenes with electrophilic amination reagents2014

    • Author(s)
      Koji Hirano
    • Journal Title

      Pure and Applied Chemistry

      Volume: 86 Issue: 3 Pages: 291-297

    • DOI

      10.1515/pac-2014-5004

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Enantioselective Formal Hydroamination of Oxa- and Azabicyclic Alkenes with Hydrosilanes and Hydroxylamines2014

    • Author(s)
      Yuya Miki
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 5 Pages: 1498-1501

    • DOI

      10.1021/ol5003219

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated Direct Arylation of Azole Compounds2014

    • Author(s)
      Koji Hirano
    • Journal Title

      Topics in Catalysis

      Volume: 印刷中 Issue: 10-13 Pages: 878-889

    • DOI

      10.1007/s11244-014-0247-y

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Electrophilic Amination of Arylsilanes with Hydroxylamines2013

    • Author(s)
      Yuya Miki
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 1 Pages: 172-175

    • DOI

      10.1021/ol303222s

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Regioselective and Stereospecific Copper-Catalyzed Aminoboration of Styrenes with Bis(pinacolato)diboron and O-Benzoyl-N,N-dialkylhydroxylamines2013

    • Author(s)
      Naoki Matsuda, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Journal of the American Chemical Society

      Volume: 135 Issue: 13 Pages: 4934-4937

    • DOI

      10.1021/ja4007645

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated C-H/C-H Biaryl Coupling of Benzoic Acid Derivatives and 1,3-Azoles2013

    • Author(s)
      Mayuko Nishino
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 16 Pages: 4457-4461

    • DOI

      10.1002/anie.201300587

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Direct Alkylation of Heterocycles with α-Bromo Carbonyl Compounds: C3-Selective Functionalization of 2-Pyridones2013

    • Author(s)
      Nakatani Akihiro, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Chemistry - A European Journal

      Volume: 19 Issue: 24 Pages: 7691-7695

    • DOI

      10.1002/chem.201301350

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Formal Anti-Markovnikov Hydroamination of Terminal Aryl Alkynes with Pinacolborane and Hydroxylamines via Zr/Cu Sequential Catalysis2013

    • Author(s)
      Ryosuke Sakae, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 10 Pages: 1128-1130

    • DOI

      10.1246/cl.130485

    • NAID

      10031201284

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Intermolecular Regioselective Hydroamination of Styrenes with Polymethylhydrosiloxane and Hydroxylamines2013

    • Author(s)
      Yuya Miki, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 41 Pages: 10830-10834

    • DOI

      10.1002/anie.201304365

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Mediated Dehydrogenative Biaryl Coupling of Naphthylamines and 1,3-Azoles2013

    • Author(s)
      Riko Odani, Koji Hirano, Tetsuya Satoh, Masahiro Miura
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 78 Issue: 21 Pages: 11045-11052

    • DOI

      10.1021/jo402078q

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Development of New Catalytic C–N Bond Formations Based on Electrophilic Amination2016

    • Author(s)
      Koji Hirano
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府、京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 銅触媒による求電子的アミノ化を利用した新規炭素―窒素結合形成2015

    • Author(s)
      Koji Hirano
    • Organizer
      ITbM/IGER Chemistry Workshop ~Symposium of Organic Chemistry by Students~
    • Place of Presentation
      名古屋大学(愛知県、名古屋市)
    • Year and Date
      2015-10-30
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Regiodivergent Copper-Catalyzed Aminoboration of Unactivated Terminal Alkenes2015

    • Author(s)
      Koji Hirano
    • Organizer
      OMCOS 18
    • Place of Presentation
      Sitges, Barcelona
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Regiodivergent Copper-Catalyzed Aminoboration of Unactivated Terminal Alkenes2015

    • Author(s)
      Koji Hirano
    • Organizer
      Organic Chemistry Symposia-Kyoto, RSC Japan Road Show
    • Place of Presentation
      京都大学(京都府、京都市)
    • Year and Date
      2015-06-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper-Catalyzed Regio- and Stereoselective Aminoboration and Hydroamination of Alkenes with Electrophilic Amination Reagents2014

    • Author(s)
      Koji Hirano
    • Organizer
      International Conference on Organometallic Chemistry (ICOMC) 2014 Post-Symposium in Osaka
    • Place of Presentation
      大阪大学(大阪府吹田市)
    • Year and Date
      2014-07-19
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Copper-Catalyzed Aminoboration of Alkenes with Bis(pinacolato)diboron and Hydroxylamines2013

    • Author(s)
      Koji Hirano
    • Organizer
      17th International IUPAC Conference on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-17)
    • Place of Presentation
      Fort Colins, USA
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 銅塩を用いた脱水素型クロスヘテロビアリールカップリング2013

    • Author(s)
      平野康次
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学、東京
    • Related Report
      2013 Research-status Report
  • [Presentation] Copper-Catalyzed Aminoboration of Alkenes with Bis(pinacolato)diboron and Hydroxylamines2013

    • Author(s)
      Koji Hirano
    • Organizer
      10th International Symposium on Carbanion Chemistry (ISCC-10)
    • Place of Presentation
      同志社大学、京都
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 求電子的アミノ化を鍵とする新規触媒的炭素-窒素結合形成反応の開発2013

    • Author(s)
      平野康次
    • Organizer
      岡山大学次世代研究者・異分野研究連携育成支援事業シンポジウム
    • Place of Presentation
      岡山大学、岡山
    • Related Report
      2013 Research-status Report
    • Invited
  • [Book] Copper-Mediated Intermolecular C-H/C-H and C-H/N-H Couplings via Aromatic C-H Cleavage in C-H Bond Activation and Catalytic Functionalization II2015

    • Author(s)
      Koji Hirano, Masahiro Miura
    • Total Pages
      18
    • Publisher
      Springer
    • Related Report
      2015 Annual Research Report
  • [Book] C-H Activation of Heteroaromatics in Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries2013

    • Author(s)
      Koji Hirano
    • Total Pages
      36
    • Publisher
      John Wiley & Sons
    • Related Report
      2013 Research-status Report
  • [Remarks] ホームページ

    • URL

      http://www.chem.eng.osaka-u.ac.jp/̃miura-lab/

    • Related Report
      2013 Research-status Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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