熊谷 直哉 (クマガイ ナオヤ)

Kumagai, Naoya



薬学部 薬科学科 分子創成化学講座 (芝共立)





経歴 【 表示 / 非表示

  • 2005年04月

    ハーバード大学, 生物化学科, ポストドクトラルフェロー

  • 2006年04月

    東京大学, 大学院薬学系研究科, 助教

  • 2010年04月

    微生物化学研究所, 有機合成研究部, 研究員

  • 2010年04月

    立教大学, 理学部, 兼任講師

  • 2011年01月

    微生物化学研究所, 有機合成研究部, 主任研究員

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学歴 【 表示 / 非表示

  • 1996年04月

    東京大学, 薬学部

    大学, 卒業

  • 2000年04月

    東京大学, 大学院薬学系研究科

    大学院, 修了, 修士

  • 2002年04月

    東京大学, 大学院薬学系研究科

    大学院, 修了, 博士

学位 【 表示 / 非表示

  • 博士(薬学), 東京大学, 課程, 2005年03月

免許・資格 【 表示 / 非表示

  • 薬剤師, 2000年09月

  • 第一種放射線管理主任者, 2012年04月


研究分野 【 表示 / 非表示

  • ナノテク・材料 / 構造有機化学、物理有機化学

  • ライフサイエンス / 生物有機化学


著書 【 表示 / 非表示

  • 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年01月


    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年


    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.

論文 【 表示 / 非表示

  • 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年09月

    ISSN  21935807


    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年08月

    ISSN  14337851


    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年07月

    ISSN  00404020


    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年05月

    ISSN  00223263


    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年02月

    ISSN  15237060


    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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KOARA(リポジトリ)収録論文等 【 表示 / 非表示

総説・解説等 【 表示 / 非表示

競争的研究費の研究課題 【 表示 / 非表示

  • 独自の分子設計を基盤とする拡張的分子機能化学の追究


    熊谷 直哉, 基盤研究(B), 補助金,  研究代表者

  • 理論化学レーダー支援による新分子骨格の迅速材料深化


    熊谷 直哉, 学術変革領域研究(B), 補助金,  研究代表者

  • ポルフィリン2.0: warped-porphyrinの化学


    文部科学省・日本学術振興会, 科学研究費助成事業, 熊谷 直哉, 挑戦的研究(萌芽), 補助金,  研究代表者

  • 戦略的分子デザインが拓く分子変換化学


    文部科学省・日本学術振興会, 科学研究費助成事業, 熊谷 直哉, 基盤研究(B), 補助金,  研究代表者

  • 一原子サイズ欠損分子トリキノリンの化学


    文部科学省・日本学術振興会, 科学研究費助成事業, 熊谷 直哉, 挑戦的研究(萌芽), 補助金,  研究代表者

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担当授業科目 【 表示 / 非表示

  • 課題研究(分子創成化学)


  • 演習(分子創成化学)


  • 卒業研究1(薬学科)


  • 英語演習(薬学科)


  • 精密有機合成


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