Kumagai, Naoya



Faculty of Pharmacy, Department of Pharmaceutical Sciences 分子創成化学講座 (Shiba-Kyoritsu)



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Career 【 Display / hide

  • 2005.04

    harvard University, Departmernt of Chemistry and Chemical Biology, Postdoctoral Fellow

  • 2006.04

    The University of Tokyo, Graduate School of Pharmaceutical Sciences, Assistant Professor

  • 2010.04

    Institute of Microbial Chemistry, Laboratory of Synthetic Organic Chemnistry, Researcher

  • 2010.04

    Rikkyo University, Department of Science, Adjunct Lecturer

  • 2011.01

    Insttitute of Microbial Chemistry, Laboratory of Synthetic Organic Chemistry, Senior Researcher

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Academic Background 【 Display / hide

  • 1996.04

    The University of Tokyo, Department of Pharmaceutical Sciences

    University, Graduated

  • 2000.04

    The University of Tokyo, Graduate School of Pharmaceutical Sciences

    Graduate School, Completed, Master's course

  • 2002.04

    The University of Tokyo, Graduate School of Pharmaceutical Sciences

    Graduate School, Completed, Doctoral course

Academic Degrees 【 Display / hide

  • The University of Tokyo, The University of Tokyo, Coursework, 2005.03

Licenses and Qualifications 【 Display / hide

  • Pharmacist, 2000.09

  • senior [first class] radiation protection supervisor, 2012.04


Research Areas 【 Display / hide

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Life Science / Bioorganic chemistry


Books 【 Display / hide

  • Interplay of diamides and rare earth metals: Specific molecular spaces and catalytic activity

    Kumagai N., Shibasaki M., Designed Molecular Space in Material Science and Catalysis, 2018.01

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    A catalytic system comprising functionalized small diamides and rare earth metals (REs) exerts intriguing catalytic properties that are dictated by dynamic construction of flexible molecular spaces. The dynamic interaction of diamides and REs is characterized by broad applicability to distinct reaction systems as well as notable switchable catalysis. Structural modification of the diamide allows for enhanced intermolecular interactions to afford a self-assembled solid-phase catalyst with a specific molecular space that engages in heterogeneous asymmetric catalysis with a continuous-flow platform.

  • Chiral Bimetallic Lewis Acids

    Shibasaki M., Kumagai N., Topics in Organometallic Chemistry, 2018

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    Here, we review the utility of chiral bimetallic (multimetallic) Lewis acidic complexes in catalytic asymmetric transformations. Bimetallic complexes are endowed with dual catalytic functions that synergistically activate multiple substrates and functionalities. This cooperative activation mode is particularly effective for activating low reactivity substrates in a highly stereoselective manner without the aid of stoichiometric activating reagents. The privileged bimetallic catalysts presented here highlight the importance of catalyst design in the development of widely applicable catalytic systems.

Papers 【 Display / hide

  • Less Is More: N(BOH)<inf>2</inf> Configuration Exhibits Higher Reactivity than the B<inf>3</inf>NO<inf>2</inf> Heterocycle in Catalytic Dehydrative Amide Formation

    Opie C.R., Noda H., Shibasaki M., Kumagai N.

    Organic Letters (Organic Letters)  25 ( 4 ) 694 - 697 2023.02

    ISSN  15237060

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    Diboron substructures have emerged as a promising scaffold for the catalytic dehydrative amidation of carboxylic acids and amines. This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)2 compound as an amidation catalyst. The new catalyst outperforms the previously reported B3NO2 heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.

  • Azo-Tagged C4N4 Fluorophores: Unusual Overcrowded Structures and Their Applications to Fluorescent Imaging

    Miki Kohei, Naoki Takizawa, Ryosuke Tsutsumi, Wei Xu, and Naoya Kumagai*

    Org. Biomol. Chem.  2023.01

    Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted

  • TEtraQuinolines: A Missing Link in the Family of Porphyrinoid Macrocycles

    Wei Xu, Yuuya Nagata, and Naoya Kumagai*

    J. Am. Chem. Soc. (Journal of the American Chemical Society)  145 ( 4 ) 2609 - 2618 2023.01

    Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted,  ISSN  00027863

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    Porphyrin contains four inwardly oriented nitrogen atoms. It is arguably the most ubiquitous multifunctional naturally occurring macrocycle that has inspired the design of novel nitrogen-containing heterocycles for decades. While cyclic tetramers of pyrrole, indole, and pyridine have been exploited as macrocycles in this category, quinoline has been largely neglected as a synthon. Herein, we report the synthesis of TEtraQuinoline (TEQ) as a ‘missing link’ in this N4 macrocycle family. In TEQs, four quinoline units are concatenated to produce an S4-symmetric architecture. TEQs are characterized by a highly rigid saddle shape, wherein the lone-pair orbitals of the four nitrogen atoms are not aligned in a planar fashion. Nevertheless, TEQs can coordinate a series of transition-metal cations (Fe2+, Co2+, Ni2+, Cu2+, Zn2+, and Pd2+). TEQs are inherently fluorescence-silent but become strongly emissive upon protonation or complexation of Zn(II) cations (ϕ = 0.71). TEQ/Fe(II) complexes can catalyze dehydrogenation and oxygenation reactions with catalyst loadings as low as 0.1 mol %.

  • Less Is More: N(BOH)2 Configuration Exhibits Higher Reactivity than the B3NO2 Heterocycle in Catalytic Dehydrative Amide Formation

    Christopher R. Opie, Hidetoshi Noda,* Masakatsu Shibasaki, and Naoya Kumagai*

    Org. Lett.  2023.01

    Research paper (scientific journal), Joint Work, Last author, Corresponding author, Accepted

  • Azo-tagged C4N4 fluorophores: unusual overcrowded structures and their application to fluorescent imaging

    Kohei M., Takizawa N., Tsutsumi R., Xu W., Kumagai N.

    Organic and Biomolecular Chemistry (Organic and Biomolecular Chemistry)  21 ( 14 )  2023

    ISSN  14770520

     View Summary

    The C4N4 fluorophore is an intense fluorescence emitter featuring a 2,5-diaminopyrimidine core comprising four carbon and four nitrogen atoms. A series of C4N4 derivatives was photochemically dimerized at the 5-amino group, furnishing overcrowded ortho-tetraaryl-substituted diaryl azo compounds with a characteristic skewed structure revealed by X-ray crystallography. The photoquenched azo-C4N4s are useful for fluorescently visualizing cells under hypoxic conditions.

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Reviews, Commentaries, etc. 【 Display / hide

Research Projects of Competitive Funds, etc. 【 Display / hide

  • Expeditious Sophistication of Seed Molecular Entities Aided by Theory and Machine Learning


    学術変革領域研究(B), Principal investigator

  • Diversification of Molecular Functions via Unique Molecular Design


    基盤研究(B), Principal investigator

  • Porphyrin 2.0: Chemistry of Warped-Porphyrin


    MEXT,JSPS, Grant-in-Aid for Scientific Research, 挑戦的研究(萌芽), Principal investigator

  • Strategic Molecular Design Aiming at Streamlined Chemical Transformations


    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), Principal investigator

  • Exploratory Study on TriQuinoline, A MInituarized Model of Graphene with Atomic-Sized Defect


    MEXT,JSPS, Grant-in-Aid for Challenging Research (Exploratory), Naoya Kumagai, Grant-in-Aid for Challenging Research (Exploratory), Principal investigator

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Courses Taught 【 Display / hide











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