Tokyo Institute of Technology,
Chemical Resources Laboratory, Smart Material Division

Interdisciplinary Graduate School of Science Engineering
Department of Environmental Chemistry Engineering

Takashi Koike

Assistant Professor


@@@ @@@ @@@ @@@ @@@ @@@ @@@ @@@ @@@ @@@
@Affiliation & Address
Laboratory for Chemistry and Life Science
Institute of Innovative Research
Tokyo Institute of Technology

AddressF4259-R27, Nagatsuta, Midori-ku, Yokohama 226-8503, Japan



(B. 1977.5.10)
2000.3@B.S.@Tokyo Institute of Technology@@@@@@@@@@@@@@@@
2002.3@M.S.@Tokyo Institute of Technology
2005.3@Ph.D.@Tokyo Institute of Technology
2005.10-2007.4@Postdoctoral Fellow, California Institute of Technology (Grubbs Lab.)
2007.5-present@Assistant Professor, Tokyo Institute of Technology

Honors & Awards
2002-2005 JSPS Research Fellowship for Young Scientists
2006 Tejima Sei-ichi Commemorative Foundation Prize for Doctoral Thesis
2009 Tejima Sei-ichi Commemorative Foundation Prize for Research Paper
2010 Mitsubishi Chemical Award in Synthetic Organic Chemistry, Japan
2015 Young Scholar Lectures of CSJ
2015 Tokyo Tech Challenging Research Award
2017 Incentive Award in Synthetic Organic Chemistry, Japan


Academic or Social Activities
2011 The 91th CSJ Annual Meeting Program Committee
2014 XXVI International Conference on Organometallic Chemistry (ICOMC 2014) Program Committee
2015 Outstanding Reviewer of ChemPubSoc Europe & ACES
2018 International CLS Forum 2018 Organizing Committee
2019 Outstanding Top 10 Reviewers of Organic Chemistry Frontiers

Invited Lectures
2014 The 11th Sagami Fluorine Seminar, Sagami Chemical Research Institute, Ayase, Japan
2015 The 22nd Biennial Winter Fluorine Conference, TradeWinds Island Grand Resort, St. Pete Beach, FL, USA
2015 The 95th CSJ Annual Meeting, Nihon University, Chiba, Japan
2015 The 3rd Young Researcher Workshop in Alliance, Kyusyu University, Fukuoka, Japan
2015 The 3rd Organic Photochemistry Seminar, Matsuyasensen, Fukui, Japan
2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015), Honolulu, HI, USA
2016 AGC Seminar, AGC research center, Yokohama, Japan
2016 The 1st International Symposium on Precisely Designed Catalysts with Customized Scaffolding, Osaka, Japan
2016 Pacific Rim Meeting on Electrochemical and Solid-State Science (PRiME 2016), Honolulu, HI, USA
2016 CSJ Tohoku-branch Seminar, Hirosaki Univ., Aomori, Japan
2017 Takasago International Corporation Seminar, Takasago research center, Hiratsuka, Japan
2017 Asian Symposium in the 97th CSJ Annual Meeting, Keio University, Yokohama, Japan
2017 Chugai Pharmaceutical Seminar, Kamakura research laboratories, Fujisawa, Japan
2018 Shionogi & CO., LTD. Seminar, Pharmaceutical Research Center, Kuise, Japan
2018 The 98th CSJ Annual Meeting, Nihon University, Chiba, Japan
2018 Toray Industries, Inc. Seminar, Pharmaceutical Research Laboratories, Kamakura, Japan
2018 The 233rd ECS Meeting, Washington State Convention Center, Seattle, WA, USA
2018 The 1st Sino-Japanese Symposium on Catalysis for Precision Synthesis, SIOC, Shanghai, China
2018 The 8th Fluorine Chemistry Seminar for Young Scientists, Fukuroda Onsen, Ibaraki, Japan
2018 The 35th Organic Synthetic Chemistry Seminar, Tendoh, Yamagata, Japan
2018 Kwansei-Gakuin Univ. Seminar, Sanda, Hyougo, Japan
2019 PSRC-9, Asilomar Conference Grounds, Monterey, CA, USA
2019 Gordon Research Conference, Stonehill College, Eaton, MA, USA
2019 CREST-Y.U.IOL Symposium, Yamaguchi Univ., Ube, Yamaguchi, Japan
2019 JSCC Conference, Nagoya Univ., Nagoya, Japan
2019 Annual Meeting on Photochemistry 2019, Nagoya Univ., Nagoya, Japan

@Recent Publications
  • Y. Nakayama, G. Ando, M. Abe, T. Koike, M. Akita
    Keto-Difluoromethylation of Aromatic Alkenes by Photoredox Catalysis: Step-Economical Synthesis of ƒΏ-CF2H-Substituted Ketones in Flow
    ACS Catal., 2019, 9, 6555-6563.


  • T. Koike, M. Akita
    Recent Progress in Photochemical Radical Di- and Mono-Fluoromethylation
    Org. Biomol. Chem., 2019, 17, 5413-5419.


  • T. Koike
    Visible-Light Photoredox Catalysis: New Strategies for Radical Reactions
    J. Synth. Org. Chem., Jpn., 2019, 77, 414-423.


  • N. Noto, T. Koike, M. Akita
    Visible Light-Triggered Monofluoromethylation of Alkenes by Strongly Reducing 1,4-Bis(diphenylamino)naphthalene Photoredox Catalysis
    ACS Catal., 2019, 9, 4382-4387.


  • T. Koike, M. Akita
    Photocatalytic Introduction of Fluorinated Groups
    Science of Synthesis: Photocatalysis in Organic Synthesis; B. Konig, Ed., 2019, 559-574.

  • M. Riou, T. Koike
    S](Trifluoromethyl)dibenzothiophenium Tetrafluoroborate
    Encyclopedia of Reagents for Organic Synthesis, 2018 (DOI: 10.1002/047084289X.rn01212.pub2)

  • N. Noto, Y. Tanaka, T. Koike, M. Akita
    Strongly Reducing (Diarylamino)anthracene Catalyst for Metal-Free Visible-Light Photocatalytic Fluoroalkylation
    ACS Catal., 2018, 8, 9408-9419.

    ACSCatal2018 ACSCatal2018_FC

  • K. Miyazawa, R. Ochi, T. Koike, M. Akita
    Photoredox Radical C|H Oxygenation of Aromatics with Aroyloxylutidinium Salts
    Org. Chem. Front., 2018, 5, 1406-1410.
    OCF2018 OCF2018_FC

  • T. Koike, M. Akita
    New Horizons of Photocatalytic Fluoromethylative Difunctionalization of Alkenes
    Chem, 2018, 4, 409-437.


  • N. Noto, T. Koike, M. Akita
    Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis
    Chem. Sci., 2017, 8, 6375-6379.


  • R. Tomita, T. Koike, M. Akita
    Photoredox-Catalyzed Oxytrifluoromethylation of Allenes: Stereoselective Synthesis of 2-Trifluoromethylated Allyl Acetates
    Chem. Commun., 2017, 53, 4681-4684.

    CC2017 CC2017_bc

  • Y. Li, T. Koike, M. Akita
    Photocatalytic Trifluoromethylthiolation of Aromatic Alkenes Associated with Hydroxylation and Alkoxylation
    Asian J. Org. Chem., 2017, 6, 445-448.

    AJOC2017 AJOC2017c

  • T. Koike, M. Akita
    Fine Design of Photoredox Systems for Catalytic Fluoromethylation of Carbon|Carbon Multiple Bonds
    Acc. Chem. Res., 2016, 49, 1937-1945.


  • T. Koike, M. Akita
    A Versatile Strategy for Difunctionalization of Carbon|Carbon Multiple Bonds by Photoredox Catalysis
    Org. Chem. Front., 2016, 3, 1345-1349.


  • K. Miyazawa, T. Koike, M. Akita
    Aminohydroxylation of Olefins with Iminopyridinium Ylides by Dual Ir Photocatalysis and Sc(OTf)3 Catalysis
    Tetrahedron, 2016, 72, 7813-7820.


  • N. Noto, T. Koike, M. Akita
    Diastereoselective Synthesis of CF3- and CF2H]Substituted Spiroethers from Aryl-Fused Cycloalkenylalkanols by Photoredox Catalysis
    J. Org. Chem., 2016, 81, 7064-7071.


  • T. Koike, M. Akita
    Combination of Organotrifluoroborates with Photoredox Catalysis Marking a New Phase in Organic Radical Chemistry
    Org. Biomol. Chem., 2016, 14, 6886-6890.
    OBC2016 OBC2016c

  • Y. Li, T. Koike, M. Akita
    Radical Pentafluorosulfanylphenylation of Styrenes by Photoredox Catalysis
    Synlett, 2016, 27, 736-740.

  • Y. Arai, R. Tomita, G. Ando, T. Koike, M. Akita
    Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols
    Chem. Eur. J., 2016, 22, 1262-1265.

  • M. Asano, R. Tomita, T. Koike, M. Akita
    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 Derivatives
    J. Fluorine Chem., 2015, 179, 83-88.

  • R. Tomita, T. Koike, M. Akita
    Photoredox-Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated Alkenes
    Angew. Chem. Int. Ed., 2015, 54, 12923-12927.

  • N. Noto, K. Miyazawa, T. Koike, M. Akita
    Anti-Diastereoselective Synthesis of CF3-Containing Spirooxazolines and Spirooxazines via Regiospecific Trifluoromethylative Spirocyclization by Photoredox Catalysis
    Org. Lett., 2015, 17, 3710-3713.

  • K. Miyazawa, T. Koike, M. Akita
    Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis
    Chem. Eur. J., 2015, 21, 11677-11680.

  • Y. Li, K. Miyazawa, T. Koike, M. Akita
    Alkyl- and Aryl-thioalkylation of Olefins with Organotrifluoroborates by Photoredox Catalysis
    Org. Chem, Front., 2015, 2, 319-323.
  • OCF2015 OCF2015c

  • T. Chinzei, K. Miyazawa, Y. Yasu, T. Koike, M. Akita
    Redox-economical Radical Generation from Organoborates and Carboxylic Acids by Organic Photoredox Catalysis
    RSC Adv., 2015, 5, 21297-21300.
  • T. Koike, M. Akita
    Visible-Light-Induced Redox Reactions by Ruthenium Photoredox Catalyst (in "Ruthenium in Catalysis")
    Top. Organomet. Chem., 2014, 48, 371-396.

  • T. Koike, M. Akita
    Recent progress in transition-metal-catalyzed trifluoromethylation of olefins using electrophilic CF3 reagents
    J. Fluorine. Chem., 2014, 167, 30-36.
  • JFC2014.jpg

  • K. Miyazawa, T. Koike, M. Akita
    Hydroaminomethylation of Olefins with Aminomethyltrifluoroborate by Photoredox Catalysis
    Adv. Synth. Catal., 2014, 356, 2749-2755.
  • ASC2014.jpg ASC2014c.jpg

  • T. Koike, M. Akita
    Visible-light radical reaction designed by Ru- and Ir-based photoredox catalysis
    Inorg. Chem. Front., 2014, 1, 562-576.
    ICF2014.jpg ICF2014c.jpg

  • R. Tomita, Y. Yasu, T. Koike, M. Akita
    Combining Photoredox-Catalyzed Trifluoromethylation and Oxidation with DMSO: Facile Synthesis of a-Trifluoromethylated Ketones from Aromatic Alkenes
    Angew. Chem. Int. Ed., 2014, 53, 7144-7148.
  • ACIE2014.jpg ACIE2014f.jpg

  • R. Tomita, Y. Yasu, T. Koike, M. Akita
    Direct C-H Trifluoromethylation of Di- and Trisubstituted Alkenes by Photoredox Catalysis (Thematic Series on "Organic Synthesis using Photoredox Catalysis")
    Beilstein J. Org. Chem., 2014, 10, 1099-1106.

  • T. Koike, M. Akita
    Trifluoromethylation by Visible-Light-Driven Photoredox Catalysis
    Top. Catal., 2014,57, 967-974 (DOI: 10.1007/s11244-014-0259-7) (Invited by ISHHC-16).

  • Y. Yasu, Y. Arai, R. Tomita, T. Koike, M. Akita
    Highly Regio- and Diastereoselective Synthesis of CF3-Substituted Lactones via Photoredox-Catalyzed Carbolactonization of Alkenoic Acids
    Org. Lett., 2014,16, 780-783 (DOI: 10.1021/ol403500y).
  • OLyasu2.jpg

  • T. Koike, M. Akita
    Visible-light-induced Photoredox Catalysis: An Easy Access to Green Radical Chemistry
    Synlett 2013, 24, 2492-2505.
  • synlett

  • K. Miyazawa, Y. Yasu, T. Koike, M. Akita
    Visible-Light-Induced Hydroalkoxymethylation of Electron-Deficient Alkenes by Photoredox Catalysis
    Chem. Commun., 2013, 49, 7249-7251 (DOI: 10.1039/c3cc42695e).
  • CCmiyazawa

  • T. Koike, M. Akita
    Photochromic Organometallics: Redox-Active Iron and Ruthenium Complexes with Photochromic DTE Ligand (Chapter 11)
    New Frontiers in Photochromism, Springer, 2013, 205-224.

  • Y. Yasu, T. Koike, M. Akita
    Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis
    Org. Lett., 2013, 15, 2136-2139 (DOI: 10.1021/ol4006272).
  • OL

  • Y. Yasu, T. Koike, M. Akita
    Visible-light-induced Synthesis of a Variety of Trifluoromethylated Alkenes from Potassium Vinyltrifluoroborates by Photoredox Catalysis
    Chem. Commun., 2013, 49, 2037-2039 (DOI: 10.1039/C3CC39235J).
  • CCyasu

  • Y. Yasu, T. Koike, M. Akita
    Visible-Light-induced Selective Generation of Radicals from Organoborates by Photoredox Catalysis
    Adv. Synth. Catal. 2012, 354, 3414-3420.
  • ASC2012

  • T. Koike, Y. Yasu, M. Akita
    Visible-light-driven Oxidation of 1,3-Dicarbonyl Compounds via Catalytic Disproportionation of TEMPO by Photoredox Catalysis
    Chem. Lett. 2012, 41, 999-1001.
  • CL2012

  • Y. Yasu, T. Koike, M. Akita
    Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts
    Angew. Chem. Int. Ed., 2012, 51, 9567-9571.
  • ACIE2012

  • Y. Yasu, T. Koike, M. Akita
    Sunlight-driven Synthesis of gamma-Diketones via Oxidative Coupling of Enamines with Silyl Enol Ethers Catalyzed by [Ru(bpy)3]2+
    Chem. Commun., 2012, 48, 5355-5357.
  • CC2012

  • M. Hatakeyama, S. Yokojima, K. Shinoda, T. Koike, M. Akita, S. Nakamura
    Theoretical Study on the Photocyclization Mechanism of Diarylethenes with Transition-Metal Substituents
    Bull. Chem. Soc. Jpn., 2012, 85, 679-686.

  • H. Li, T. Koike, and M. Akita
    Color Change of Redox-active Organometallic Dithienylethene Complexes by Photochemical and Redox Processes
    Dyes and Pigments 2012, 92, 854-860.

  • K. Motoyama, H. Li, T. Koike, M. Hatakeyama, S. Yokojima, S. Nakamura, and M. Akita
    Photo- and Electro-chromic Organometallics with Dithienylethene (DTE) Linker, L2CpM-DTE-MCpL2: Dually Stimuli-Responsive Molecular Switch
    Dalton Trans., 2011, 40, 10643-10657 (Dalton Trans. 40th anniversary issue).

  • K. Johno, Y. Tanaka, T. Koike, and M. Akita
    Making Organometallic Molecular Wire via Oxidative Ligand Coupling
    Dalton Trans., 2011, 40, 8089-8091.

  • A. Gondoh, T. Koike, and M. Akita
    3,5-Bis(diphenylphosphinoethyl)pyrazolate ligand (PNNPC2) and its dirhodium complexes: comparison with related quadridentate dinucleating diphenylphosphinomethyl (PNNPPy) and phthalazine derivatives (PNNPPh)
    Inorg. Chim. Acta 2011, 374, 489-498. (special issue dedicated to Prof. W. Kaim).

  • T. Yamaguchi, T. Koike, and M. Akita
    Dirhodium Complexes Bridged by Bis(diphenylphosphino)phthalazine (PNNPPh): Central Ring Size and Charge Effects as Compared with the Pyrazolate Derivative (PNNPPy)
    Organometallics, 2010, 29, 6493|6502.

  • Y. Tanaka, T. Koike, and M. Akita
    Reversible, Fine Performance Tuning of Organometallic Molecular Wire by Addition, Ligand Replacement and Removal of Dicobalt Fragments
    Eur. J. Inorg. Chem., 2010, 23, 3571-3575 .

  • Y. Tanaka, T. Koike, and M. Akita
    2-Dimensional molecular wiring based on toroidal delocalization of hexaarylbenzene.
    Chem. Commun., 2010, 46, 4529-4531.

  • Y. Tanaka, T. Ishisaka, A. Inagaki, T. Koike, C. Lapinte, and M. Akita
    Photochromic Organometallics with a Dithienylethene (DTE) Bridge, M-CC-DTE-CC-M [M= MCp*(dppe)]: Photoswitchable Molecular Wire (M= Fe) vs. Dual Photo- and Electro-chromism (M= Ru).
    Chem. Eur. J., 2010, 16, 4762-4776.

  • T. Koike, M. Akita
    Photoinduced Oxyamination of Enamines and Aldehydes with TEMPO Catalyzed by [Ru(bpy)3]2+
    Chem. Lett., 2009, 38, 166|167.

  • S. Arita, T. Koike, Y. Kayaki, T. Ikariya
    Aerobic Oxidation of Alcohols with Bifunctional Transition Metal Catalysts Bearing C-N Chelate Ligands
    Chem. Asian J., 2008, 3, 1479|1485.

  • S. Arita, T. Koike, Y. Kayaki, T. Ikariya
    Synthesis and Reactivities of Cp*Ir Amide and Hydride Complexes Bearing C-N Chelate Ligands
    Organometallics, 2008, 27, 2795|2802.

  • S. Arita, T. Koike, Y. Kayaki, T. Ikariya
    Aerobic Oxidative Kinetic Resolution of Racemic Secondary Alcohols with Chiral Bifunctional Amido Complexes
    Angew. Chem. Int. Ed., 2008, 47, 2447-2449 (selected as "Very Important Papers").

  • T. Koike, T. Ikariya
    Synthesis and Properties of Alkylruthenium Complexes Bearing Primary and Secondary Amine Ligands
    J. Organomet. Chem., 2007, 692, 408-419.

  • T. Koike, T. Ikariya
    Reaction of 16-Electron Ruthenium and Iridium Amide Complexes with Acidic Alcohols: Intramolecular C-H Bond Activation and the Isolation of Cyclometalated Complexes
    Organometallics, 2005, 24, 724-730.

  • T. Koike, T. Ikariya
    Mechanistic Aspects of Formation of Chiral Ruthenium Hydride Complexes from 16-Electron Ruthenium Amide Complexes and Formic Acid: Facile Reversible Decarboxylation and Carboxylation
    Adv. Synth. Catal., 2004, 346, 37-41.

  • T. Koike, K. Murata, T. Ikariya
    Stereoselective Synthesis of Optically Active ƒΏ-Hydroxy Ketones and anti-1,2-Diols via Asymmetric Transfer Hydrogenation of Unsymmetrically Substituted 1,2-Diketones
    Org. Lett., 2000, 2, 3833-3836.