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New molecular transformations via radical species based on photoredox catalysis

Research Project

Project/Area Number 26288045
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Akita Munetaka  東京工業大学, 科学技術創成研究院, 教授 (50167839)

Co-Investigator(Kenkyū-buntansha) 小池 隆司  東京工業大学, 資源化学研究所, 助教 (30451991)
Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥16,640,000 (Direct Cost: ¥12,800,000、Indirect Cost: ¥3,840,000)
Fiscal Year 2017: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2016: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2015: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2014: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Keywordsフォトレドックス触媒反応 / ラジカル反応光反応 / 可視光 / フッ素化反応 / フォトレドックス触媒 / 二官能基化 / 合成化学 / フルオロアルキル化 / 光化学 / 触媒反応 / ラジカル反応 / 光反応 / 有機フッ素化合物
Outline of Final Research Achievements

“Photoredox catalysis”, where versatile organic radicals species are generated by the action of one-electron transfer processes mediated by photo-activated catalysts, has attracted much attention from the viewpoint of “Green Chemistry” but much room remains to be studied such as development of new transformations, new precursors, and various types of catalysts. Our attention has been paid to the following aspects, which have been solved by the present study: development of i) regiospecific olefin difunctionalization, ii) design and synthesis of new precursors for various organic radicals, and iii) organic catalysts.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (51 results)

All 2018 2017 2016 2015 2014 Other

All Journal Article (23 results) (of which Peer Reviewed: 23 results,  Acknowledgement Compliant: 14 results,  Open Access: 7 results) Presentation (20 results) (of which Int'l Joint Research: 7 results,  Invited: 12 results) Book (1 results) Remarks (3 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] New Horizons of Photocatalytic Fluoromethylative Difunctionalization of Alkenes2018

    • Author(s)
      Koike Takashi、Akita Munetaka
    • Journal Title

      Chem

      Volume: 4 Issue: 3 Pages: 409-437

    • DOI

      10.1016/j.chempr.2017.11.004

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photocatalytic Trifluoromethylthiolation of Aromatic Alkenes Associated with Hydroxylation and Alkoxylation2017

    • Author(s)
      Yanjie Li, Takashi Koike, Munetaka Akita
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 6 Issue: 4 Pages: 445-448

    • DOI

      10.1002/ajoc.201600562

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Photoredox-catalyzed oxytrifluoromethylation of allenes: stereoselective synthesis of 2-trifluoromethylated allyl acetates2017

    • Author(s)
      Ren Tomita, Takashi Koike, Munetaka Akita
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 34 Pages: 4681-4684

    • DOI

      10.1039/c7cc01759f

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis2017

    • Author(s)
      Noto Naoki、Koike Takashi、Akita Munetaka
    • Journal Title

      Chemical Science

      Volume: 8 Issue: 9 Pages: 6375-6379

    • DOI

      10.1039/c7sc01703k

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols2016

    • Author(s)
      Ren Tomita, Gaku Ando, Yusuke Arai, Takashi Koike and Munetaka Akita
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Pages: 1262-1265

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Radical Pentafluorosulfanylphenylation of Styrenes by Photoredox Catalysis2016

    • Author(s)
      Yanjie Li, Takashi Koike and Munetaka Akita
    • Journal Title

      Synlett

      Volume: 27 Issue: 05 Pages: 736-740

    • DOI

      10.1055/s-0035-1561304

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Aminohydroxylation of Olefins with Iminopyridinium Ylides by Dual Ir Photocatalysis and Sc(OTf)3 Catalysis2016

    • Author(s)
      宮澤和己、小池隆司、穐田宗隆
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 48 Pages: 7813-7820

    • DOI

      10.1016/j.tet.2016.05.045

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Diastereoselective Synthesis of CF3- and CF2H‐Substituted Spiroethers from Aryl-Fused Cycloalkenylalkanols by Photoredox Catalysis2016

    • Author(s)
      Naoki Noto, Takashi Koike, Munetaka Akita
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 81 Issue: 16 Pages: 7064-7071

    • DOI

      10.1021/acs.joc.6b00953

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Fine Design of Photoredox Systems for Catalytic Fluoromethylation of Carbon-Carbon Multiple Bonds2016

    • Author(s)
      Takashi Koike, Munetaka Akita
    • Journal Title

      Accounts of Chemical Research

      Volume: 49 Issue: 9 Pages: 1937-1945

    • DOI

      10.1021/acs.accounts.6b00268

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Combination of Organotrifluoroborates with Photoredox Catalysis Marking a New Phase in Organic Radical Chemistry2016

    • Author(s)
      Takashi Koike, Munetaka Akita
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 14 Issue: 29 Pages: 6886-6890

    • DOI

      10.1039/c6ob00996d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Versatile Strategy for Difunctionalization of Carbon-Carbon Multiple Bonds by Photoredox Catalysis2016

    • Author(s)
      Takashi Koike, Munetaka Akita
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 3 Issue: 10 Pages: 1345-1349

    • DOI

      10.1039/c6qo00139d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Principles and Applications of Photoredox Catalysis:Trifluoromethylation and Beyond2016

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 74 Issue: 11 Pages: 1036-1046

    • DOI

      10.5059/yukigoseikyokaishi.74.1036

    • NAID

      130005433328

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Sunlight-Driven Trifluoromethylation of Olefinic Substrates by Photoredox Catalysis: A Green Organic Process2015

    • Author(s)
      M. Akita, T. Koike
    • Journal Title

      Compt. Rend. Chim.

      Volume: 18 Issue: 7 Pages: 742-751

    • DOI

      10.1016/j.crci.2015.01.013

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Redox-economical radical generation from organoborates and carboxylic acids by organic photoredox catalysis2015

    • Author(s)
      Tatsuya Chinzei, Kazuki Miyazawa, Yusuke Yasu, Takashi Koike, Munetaka Akita
    • Journal Title

      RSC Advances

      Volume: 5 Issue: 27 Pages: 21297-21300

    • DOI

      10.1039/c5ra01826a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Alkyl- and Aryl-Thioalkylation of Olefins with Organotrifluoroborates by Photoredox Catalysis2015

    • Author(s)
      Y. Li, K. Miyazawa, T. Koike, M. Akita
    • Journal Title

      Org. Chem. Front.

      Volume: 2 Issue: 4 Pages: 319-323

    • DOI

      10.1039/c4qo00352g

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Anti-Diastereoselective Synthesis of CF3-Containing Spirooxazolines and Spirooxazines via Regiospecific Trifluoromethylative Spirocyclization by Photoredox Catalysis2015

    • Author(s)
      N. Noto, K. Miyazawa, T. Koike, M. Akita
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 15 Pages: 3710-3713

    • DOI

      10.1021/acs.orglett.5b01694

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis2015

    • Author(s)
      Kazuki Miyazawa, Takashi Koike, Munetaka Akita
    • Journal Title

      Chemistry -A European Journal

      Volume: 21 Issue: 33 Pages: 11677-11680

    • DOI

      10.1002/chem.201501590

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Photoredox-Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated Alkenes2015

    • Author(s)
      Ren Tomita, Gaku Ando, Takashi Koike, Munetaka Akita
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 54 Issue: 44 Pages: 12923-12927

    • DOI

      10.1002/anie.201505550

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Trifluoromethylation of Aromatic Alkenes by Visible-light-driven Photoredox Catalysis: Direct Conversion of Alkenes to 3-Trifluoromethyl-1-propenyl and 1,3-Bis(trifluoromethyl)-1-propenyl Derivatives2015

    • Author(s)
      Masahiro Asano, Ren Tomita, Gaku Ando, Takashi Koike, Munetaka Akita
    • Journal Title

      Journal of Fluorine Chemistry

      Volume: 179 Pages: 83-88

    • DOI

      10.1016/j.jfluchem.2015.07.020

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydroaminomethylation of Olefins with Aminomethyltrifluoroborate by Photoredox Catalysis2014

    • Author(s)
      Kazuki Miyazawa, Takashi Koike, and Munetaka Akita
    • Journal Title

      Adv. Synth. Cat.

      Volume: 356 Issue: 13 Pages: 2749-2755

    • DOI

      10.1002/adsc.201400556

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Combining Photoredox-Catalyzed Trifluoromethylation and Oxidation with DMSO : Facile Synthesis of a-Trifluoromethylated Ketones from Aromatic Alkenes2014

    • Author(s)
      Ren Tomita, Yusuke Yasu, Takashi Koike, Munetaka Akita
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 53 Issue: 28 Pages: 7144-7148

    • DOI

      10.1002/anie.201403590

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct C-H Trifluoromethylation of Di- and Trisubstituted Alkenes by Photoredox Catalysis2014

    • Author(s)
      Ren Tomita, Yusuke Yasu, Takashi Koike, Munetaka Akita
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 10 Pages: 1099-1106

    • DOI

      10.3762/bjoc.10.108

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Highly Regio- and Diastereoselective Synthesis of CF3-Substituted Lactones via Photoredox-Catalyzed Carbolactonization of Alkenoic Acids2014

    • Author(s)
      Yusuke Yasu, Yusuke Arai, Ren Tomita, Takashi Koike, Munetaka Akita
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 3 Pages: 780-783

    • DOI

      10.1021/ol403500y

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Presentation] Photoredox Catalysis: Trifluoromethylation and Beyond2017

    • Author(s)
      Munetaka Akita
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Olefin Difunctionalization by Photoredox Catalysis2017

    • Author(s)
      Munetaka Akita
    • Organizer
      the 8th Pacific Symposium on Radical Chemistry (PSRC-8)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Fluoromethylative Difunctionalization of Unsaturated Hydrocarbons by Photoredox Catalysis2017

    • Author(s)
      Munetaka Akita
    • Organizer
      the 18th Tetrahedron Symposium Asian Edition
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Olefin Difunctionalization by Photoredox Catalysis2017

    • Author(s)
      Munetaka Akita
    • Organizer
      the 6th Gratama Workshop on Chemical Sciences and Innovation for a Sustainable Society
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photoredox Catalysis: Trifluoromethylation and Beyond2016

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      Conference on Frontiers of Organometallic Chemistry - 2016 (FOMC-2016)
    • Place of Presentation
      ケラーラ、 インド
    • Year and Date
      2016-12-03
    • Related Report
      2016 Annual Research Report
  • [Presentation] Photoredox Catalysis: A Green Catalytic System Promoted by Visible Light2016

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2016 (C&FC 2016)
    • Place of Presentation
      台北、 台湾
    • Year and Date
      2016-11-03
    • Related Report
      2016 Annual Research Report
  • [Presentation] Photoredox Catalysis: Trifluoromethylation and Beyond2016

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      17th Korea-Japan Inorganic Chemistry Joint Symposium
    • Place of Presentation
      釜山、韓国
    • Year and Date
      2016-11-03
    • Related Report
      2016 Annual Research Report
  • [Presentation] Generation of Organyl Radicals via Photoredox Catalysis: Regiospecific Difunctionalization of Olefins and Acetylenes2016

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      12th International Symposium on Organic Free Radicals (ISOFR-12)
    • Place of Presentation
      上海、中国
    • Year and Date
      2016-10-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] フォトレドックス触媒反応:可視光(太陽光)で促進される有機電子移動触媒反応2016

    • Author(s)
      穐田宗隆
    • Organizer
      分子研研究会「有機金属化学の大潮流」
    • Place of Presentation
      分子科学研究所
    • Year and Date
      2016-09-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] Photoredox Catalysis: Trifluoromethylation and Beyond2016

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      the 27th International Conference on Organometallic Chemistry (ICOMC2016)
    • Place of Presentation
      メルボルン、オーストラリア
    • Year and Date
      2016-07-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Inorganic Photoredox Catalysis Applied to Organic Synthesis: Trifluoromethylation of Unsaturated Hydrocarbons2016

    • Author(s)
      Munetaka Akita
    • Organizer
      the 42nd International Conference on Coordination Chemistry (ICCC2016)
    • Place of Presentation
      ブレスト、フランス
    • Year and Date
      2016-07-03
    • Related Report
      2016 Annual Research Report
  • [Presentation] Trifluoromethylation of olefins by photoredox catalysis2015

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      pacifichem2015
    • Place of Presentation
      ハワイ
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical Functionalization of Olefins via Photoredox Catalysis: Trifluoromethylation and Beyond2015

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      7th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      シンガポール 南洋大学
    • Year and Date
      2015-07-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Inorganic Photoredox Catalysis Applied to Organic Synthesis: a Green Method for Generation of Organic Radicals2015

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      5th Asian Conference on Coordination Chemistry
    • Place of Presentation
      香港大学
    • Year and Date
      2015-07-12
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] フォトレドックス触媒反応:太陽光で進む触媒的有機反応の開発2014

    • Author(s)
      穐田宗隆、小池隆司
    • Organizer
      第47回酸化反応討論会
    • Place of Presentation
      崇城大学市民ホール(熊本県・熊本市)
    • Year and Date
      2014-11-14 – 2014-11-15
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Photoredox Catalysis: A Green Access to Radical Chemistry2014

    • Author(s)
      穐田宗隆
    • Organizer
      有機金属および配位化学に関する日韓合同シンポジウム
    • Place of Presentation
      さくらホール、東北大学(宮城県・仙台市)
    • Year and Date
      2014-10-23 – 2014-10-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Photoredox Catalysis: Organic Synthesis Promoted by Visible Light2014

    • Author(s)
      Munetaka Akita
    • Organizer
      Europe-Japan Joint Forum; Inorganic Chemistry and Its Interfaces
    • Place of Presentation
      ストラスブール(フランス)
    • Year and Date
      2014-10-16 – 2014-10-17
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] フォトレドックス触媒反応:太陽光で進む有機反応の開発2014

    • Author(s)
      穐田宗隆
    • Organizer
      第114回触媒討論会
    • Place of Presentation
      広島大学(広島県・東広島市)
    • Year and Date
      2014-09-25 – 2014-09-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Trifluoromethylation by Sunlight-promoted photoredox Catalysis2014

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      Molecular Complexity in Modern Chemistry (MCMC-2014)
    • Place of Presentation
      モスクワ(ロシア)
    • Year and Date
      2014-09-13 – 2014-09-19
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Trifluoromethylation by Photoredox Catalysis2014

    • Author(s)
      Munetaka Akita and Takashi Koike
    • Organizer
      The 248th American Chemical Society Meeting & Exposition
    • Place of Presentation
      サンフランシスコ(アメリカ)
    • Year and Date
      2014-08-12
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Book] Visible-Light-Induced Redox Reactions by Ruthenium Photoredox Catalyst2014

    • Author(s)
      Takashi Koike and Munetaka Akita
    • Total Pages
      25
    • Publisher
      Springer
    • Related Report
      2014 Annual Research Report
  • [Remarks] 穐田・吉沢研究室(錯体化学・超分子科学)

    • URL

      http://www.res.titech.ac.jp/~smart/smartj.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] 穐田・吉沢研究室ホームページ

    • URL

      http://www.res.titech.ac.jp/~smart/smartj.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] 穐田・吉沢研究室

    • URL

      http://www.res.titech.ac.jp/~smart/smartj.html

    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] 多環芳香族炭化水素を光触媒とするフルオロメチル基含有化合物の製造方法2017

    • Inventor(s)
      納戸直木・小池隆司・穐田宗隆
    • Industrial Property Rights Holder
      東京工業大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017
    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] 多環芳香族炭化水素を光触媒とするフルオロメチル基含有化合物の製造方法2017

    • Inventor(s)
      納戸直木・小池隆司・穐田宗隆
    • Industrial Property Rights Holder
      納戸直木・小池隆司・穐田宗隆
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017-02-20
    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] ジフルオロメチル基含有アルコールの製造方法2015

    • Inventor(s)
      新井悠亮・小池隆司・穐田宗隆
    • Industrial Property Rights Holder
      新井悠亮・小池隆司・穐田宗隆
    • Industrial Property Rights Type
      特許
    • Filing Date
      2015-03-09
    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] 1,2-アミノアルコール骨格を持つ化合物の製造方法2014

    • Inventor(s)
      宮澤和己・小池隆司・穐田宗隆
    • Industrial Property Rights Holder
      東京工業大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-11-27
    • Related Report
      2014 Annual Research Report

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Published: 2014-04-04   Modified: 2019-03-29  

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