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

  • Chemoselective Catalytic Dehydrogenation of Benzylic Amines Driven by the TEtraQuinoline/FeCl<inf>2</inf> Complex

    Nishiwaki M., Xu W., Kumagai N.

    Asian Journal of Organic Chemistry (Asian Journal of Organic Chemistry)  12 ( 9 )  2023.09

    ISSN  21935807

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    A chemoselective dehydrogenation protocol for benzylic amines catalyzed by the TEtraQuinoline (TEQ)/FeCl2 complex is described. In combination with 2 equiv of tert-butyl hydroperoxide, as little as 0.1 mol% of catalyst loading was sufficient to convert primary and secondary benzylic amines to the corresponding imines and dimerized imines, respectively. Subsequent hydrolysis of the imines allowed for removal of the benzyl group on the nitrogen atom. Nonaromatic carbon-carbon multiple bonds and the O-Bn group remained intact in the present protocol, providing a complementary deprotection procedure to reductive removal conditions exerted by Pd catalysis.

  • Oxa-TriQuinoline: A New Entry to Aza-Oxa-Crown Architectures**

    Kobayashi T., Kumagai N.

    Angewandte Chemie - International Edition (Angewandte Chemie - International Edition)  62 ( 32 )  2023.08

    ISSN  14337851

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    A new 15-membered-macrocyclic molecular entity, oxa-TriQuinoline (o-TQ), was designed and synthesized. In o-TQ, three oxygen atoms were joined onto three quinoline units at the 2- and 8-positions in a head-to-tail fashion by three-fold SNAr reactions, giving rise to the characteristic N3O3 aza-oxa-crown architecture. o-TQ can serve as a new tridentate nitrogen ligand to capture a CuI cation and adopt a bowl shape, before supramolecular complexation with corannulene and [12]cycloparaphenylene (CPP) occurs through π–π and CH–π interactions. In the presence of the CuI cation, the non-emissive o-TQ becomes a highly emissive material in the solid state, whereby the emission wavelengths depend on the ancillary ligand on the CuI cation. The o-TQ/CuI complex is able to promote carbene catalysis to provide a range of enamines with a gem-difluorinated terminus.

  • A brief introduction to highly symmetric N-heteroarene-based macrocycles

    Xu W., Kumagai N.

    Tetrahedron (Tetrahedron)  141 2023.07

    ISSN  00404020

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    Nitrogen-containing macrocycles have attracted sustained attention because of their fascinating structures and extensive applications in organic chemistry, therapeutic developments, and materials science. The nitrogen atoms in the macrocycles play important roles in the interaction with metal cations or small molecules, endowing their potential in catalysis, fluorescent sensors, and host–guest chemistry. In this context, herein we summarize highly symmetric nitrogen-containing N3/N4/N6 macrocycles comprising pyrroles, pyridines, quinolines, and (iso)indoles as key N-heteroarenes. The direct and indirect connectivity of N-heteroarene subunits allows for the construction of both flat and non-flat cyclic architectures. The synthesis, structure, and properties of these macrocycles are highlighted.

  • Expeditious Access to the B<inf>3</inf>NO<inf>2</inf> Heterocycle Enabling Modular Derivatization

    Tsutsumi R., Kashiwagi N., Kumagai N.

    Journal of Organic Chemistry (Journal of Organic Chemistry)  88 ( 9 ) 6247 - 6251 2023.05

    ISSN  00223263

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    DATB (1,3-dioxa-5-aza-2,4,6-triborinane) is a unique six-membered heterocycle exhibiting proficient catalytic activity in direct dehydrative amidation. Reported herein is an improved synthetic protocol for DATB derivatives featuring a concise two-step chromatography-free process. Suzuki-Miyaura coupling assembled 2,6-dibromoaniline derivatives and 1,2-phenylenediboronic acid to afford dimeric B-spiroborate salts. Acidic untying of the spiroborates gave rise to the DATB ring system with various substituents.

  • 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.

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Papers, etc., Registered in KOARA 【 Display / hide

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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