Research activity information

• Nov. 2024, 日本化学会北海道支部, 支部奨励賞
  フローマイクロ合成化学に立脚した高反応性化学種の自在制御法の開拓
  芦刈洋祐
• Nov. 2020, 有機合成化学協会, 関東化学 研究企画賞
  バイメタリックアレーン類のフローマイクロ合成と金属選択的カップリング反応への展開
  芦刈洋祐
• Apr. 2013, 日本化学会, 第93春季年会学生講演賞
• Jun. 2008, 第32回有機電子移動化学討論会 優秀ポスター賞

• Anion Mask Strategy Enabling Organolithium Species Bearing Formyl Groups: Protecting-Group-Free Synthesis for Unsymmetric Dicarbonyl Arenes
  Yosuke Ashikari; Ryuhei Kikuchi; Moe Adachi; Hiroki Soutome; Aiichiro Nagaki
  The Journal of Organic Chemistry, 23 Apr. 2026
  Scientific journal
• One-Shot Reaction: Controlling Ultrafast Reactions in Coexistence Flow Conditions
  Yosuke Ashikari; Masatomo Iwata; Aiichiro Nagaki
  05 Apr. 2026
• O‐C Glycoside Rearrangement through Time‐Controlled Electrochemical Flow Strategy: Switching between Kinetics and Thermodynamics
  Yosuke Ashikari; Yiyue Yao; Takuma Kudo; Masahiro Takumi; Aiichiro Nagaki
  European Journal of Organic Chemistry, 27 May 2025
  Scientific journal
• Sequence‐Defined Synthesis Enabled by Fast and Living Anionic Monoaddition of Vinyl Monomers
  Kazuhiro Okamoto; Dong‐eun Yoo; Rikako Yoshioka; Ryohei Nakasato; Yosuke Ashikari; Kenji Kitayama; Aiichiro Nagaki
  Angewandte Chemie International Edition, 21 Jan. 2025
  Scientific journal
• Sequence‐Defined Synthesis Enabled by Fast and Living Anionic Monoaddition of Vinyl Monomers
  Kazuhiro Okamoto; Dong‐eun Yoo; Rikako Yoshioka; Ryohei Nakasato; Yosuke Ashikari; Kenji Kitayama; Aiichiro Nagaki
  Angewandte Chemie, 21 Jan. 2025
  Scientific journal
• Generation and Reaction of Benzyl Triflates by Anodic Oxidation of Toluenes
  Yosuke ASHIKARI; Takuma KUDO; Aiichiro NAGAKI
  Electrochemistry, 2025
  Scientific journal
• Continuous flow synthesis of cyclobutenes via lithium ynolates
  Aki Kohyama; Motoki Namioka; Hiroshi Naka; Yosuke Ashikari; Aiichiro Nagaki; Hiroshi Takikawa; Yousuke Yamaoka; Kiyosei Takasu
  Green Chemistry, 2025
  Scientific journal
• Anionic polymerization driven by flow microchemistry
  Aiichiro Nagaki; Yosuke Ashikari
  Polymer Journal, 57, 2, 143, 148, Springer Science and Business Media LLC, 14 Nov. 2024, [Peer-reviewed], [Invited]
  Scientific journal
• Expanding the Scope of C-Glycoside Synthesis from Unstable Organolithium Reagents Using Flow Microreactors
  Hiromichi V. Miyagishi; Yusuke Kimuro; Yosuke Ashikari; Aiichiro Nagaki
  Organic Letters, 14 Jun. 2024
  Scientific journal
• Convergent approach for direct cross-coupling enabled by flash irreversible generation of cationic and anionic species
  Hiroki Soutome; Hiroki Yamashita; Yutaka Shimizu; Masahiro Takumi; Yosuke Ashikari; Aiichiro Nagaki
  Nature Communications, 15, 1, Springer Science and Business Media LLC, 13 Jun. 2024
  Scientific journal, Abstract
  
  In biosynthesis multiple kinds of reactive intermediates are generated, transported, and reacted across different parts of organisms, enabling highly sophisticated synthetic reactions. Herein we report a convergent synthetic approach, which utilizes dual intermediates of cationic and carbanionic species in a single step, hinted at by the ideal reaction conditions. By reactions of unsaturated precursors, such as enamines, with a superacid in a flow microreactor, cationic species, such as iminium ions, are generated rapidly and irreversibly, and before decomposition, they are transported to react with rapidly and independently generated carbanions, enabling direct C-C bond formation. Taking advantage of the reactivity of these double reactive intermediates, the reaction take place within a few seconds, enabling synthetic reactions which are not applicable in conventional reactions.
• Fully Automated Reaction Operation Driven by Accurate Inline FTIR Analysis based on Linear-Combination Strategy
  Yosuke Ashikari; Takashi Tamaki; Kyosuke Tomite; Yuya Yonekura; aiichiro nagaki
  American Chemical Society (ACS), 17 May 2024
  To accelerate advancements in organic chemistry research and development, we propose a fully automated system based on real-time inline analysis performed by Fourier-transform infrared spectroscopy and assisted by a neural network model. To rapidly collect data, a linear combination of spectral intensities was used as training data for a yield prediction model. Using this model, we demonstrated real-time yield prediction of Suzuki-Miyaura cross-coupling with remarkable accuracy. By combining this yield prediction model with real-time inline analysis and a flow chemistry setup, we have developed a fully automated system for the rapid and efficient optimization of reaction conditions and process analysis.
• Highly Productive Flow Synthesis for Lithiation, Borylation, and/or Suzuki Coupling Reaction
  Hiroki Soutome; Kei Maekawa; Yosuke Ashikari; Aiichiro Nagaki
  Organic Process Research & Development, 17 May 2024
  Scientific journal
• Flash Sequence-Defined Molecular Synthesis Enabled by Living Anionic Monoaddition of Polymerizable Alkenes
  Kazuhiro Okamoto; Dong-eun Yoo; Rikako Yoshioka; Ryohei Nakasato; Yosuke Ashikari; Kenji Kitayama; aiichiro nagaki
  15 Apr. 2024
• Flowmicro In‐Line Analysis‐Driven Design of Reactions Mediated by Unstable Intermediates: Flash Monitoring Approach
  Yosuke Ashikari; Rikako Yoshioka; Yuya Yonekura; Dong‐eun Yoo; Kazuhiro Okamoto; Aiichiro Nagaki
  Chemistry – A European Journal, 25 Mar. 2024
  Scientific journal
• Elucidation of the kinetic stabilities of carbenoid species by integration of theoretical and experimental studies
  Kazuhiro Okamoto; Kensuke Muta; Hidetaka Yamada; Ryosuke Higuma; Yosuke Ashikari; Aiichiro Nagaki
  Reaction Chemistry & Engineering, 2024
  Scientific journal
• 機械学習を活用したフローリアクター合成のプロセス最適化、自動化
  芦刈洋祐; 永木愛一郎
  MATERIAL STAGE, 23, 9, 41, 45, Dec. 2023, [Peer-reviewed], [Invited], [Lead author]
• One-Flow Operation via 4-Bromopyridine Enables Flash Synthesis of AChE Inhibitor
  Hiroki Soutome; Yusuke Kimuro; Tomoko Kawaguchi; Dong-eun Yoo; Yiyue Yao; Shuto Oshida; Hiroki Nakayama; Masatomo Iwata; Ruka Ebisawa; Ryuhei Kikuchi; Kyosuke Tomite; Shuto Wada; Yosuke Ashikari; Aiichiro Nagaki
  Synthesis, Georg Thieme Verlag KG, 28 Nov. 2023, [Peer-reviewed]
  Scientific journal, Abstract
  
  4-Bromopyridine is a building block that can be converted into valuable compounds, but due to its low stability, it is commercially available in the form of hydrochloride salt. Therefore, the hydrochloride salt is usually desalted with a basic aqueous solution and dried before organic reaction. In this study, to simplify the preparation and reaction procedure of 4-bromopyridine, multiple operations, desalting with a base, separation of the aqueous layer, and subsequent halogen–lithium exchange reaction were integrated into a single flow reaction. The reaction sequence was completed within 20 seconds and the yields were higher than the conventional methods. This is because the subsequent reaction can be performed immediately after the generation of 4-bromopyridine, which is unstable under ambient conditions.
• Electrocatalytic Reduction of (Hetero)Aryl Halides in a Proton‐Exchange Membrane Reactor and its Application for Deuteration
  Yosuke Ashikari; Kyoko Mandai; Yiyue Yao; Yuta Tsuchihashi; Aiichiro Nagaki
  ChemElectroChem, 10, 23, Wiley, 12 Sep. 2023, [Peer-reviewed], [Lead author]
  Scientific journal, Abstract
  
  We developed an electrocatalytic reduction of (hetero)aryl halides under mild conditions using a proton exchange membrane (PEM) reactor. This approach allows substituting the halogeno groups on the aryl rings to protons by water and electron. Taking advantage of this transformation, deuterodehalogenation of (hetero)aryl halides, which forms mono‐deuterated (hetero)aryls, was demonstrated using heavy water as a deuterium source. The current efficiency and deuterium ratio could be increased by the conditions optimized by machine‐learning method, Bayesian optimization.
• Continuous enantiomeric separation using water-oil-water segmented flow system
  Yosuke Muranaka; Taisuke Maki; Daiki Nakayoshi; Shusaku Asano; Katsuya Ikebata; Aiichiro Nagaki; Yosuke Ashikari; Kyoko Mandai; Kazuhiro Mae
  Chemical Engineering Journal, 469, 143891, 143891, Elsevier BV, Aug. 2023, [Peer-reviewed]
  Scientific journal
• External Flash Generation of Carbenoids Enables Monodeuteration of Dihalomethanes
  Kazuhiro Okamoto; Ryosuke Higuma; Kensuke Muta; Keita Fukumoto; Yuta Tsuchihashi; Yosuke Ashikari; Aiichiro Nagaki
  Chemistry – A European Journal, 29, 47, Wiley, 18 Jul. 2023, [Peer-reviewed]
  Scientific journal, Abstract
  
  In this study, incorporation of one deuterium atom was achieved by H−D exchange of one of the two identical methylene protons in various dihalomethanes (halogen=Cl, Br, and I) through a rapid‐mixing microflow reaction of lithium diisopropylamide as a strong base and deuterated methanol as a deuteration reagent. Generation of highly unstable carbenoid intermediate and suppression of its decomposition were successfully controlled under high flow‐rate conditions. Monofunctionalization of diiodomethane afforded various building blocks composed of boryl, stannyl, and silyl groups. The monodeuterated diiodomethane, which served as a deuterated C1 source, was subsequently subjected to diverted functionalization methods to afford various products including biologically important molecules bearing isotope labelling at specific positions and homologation products with monodeuteration.
• Flash functional group-tolerant biaryl-synthesis based on integration of lithiation, zincation and negishi coupling in flow
  Yosuke Ashikari; Kaiteng Guan; Aiichiro Nagaki
  Frontiers in Chemical Engineering, 4, Frontiers Media SA, 22 Jul. 2022, [Peer-reviewed], [Lead author]
  Scientific journal, We achieved an integration of a lithiation of aryl bromides, a zincation of thus-generated aryllithiums, and a Negishi coupling of the arylzinc with an aryl halide in one flow. Taking advantages of flow microreactors, biaryls bearing a wide range of functional groups, especially biaryls bearing multiple electrophilic-functionalities were synthesized.
• Flow grams-per-hour production enabled by hierarchical bimodal porous silica gel supported palladium column reactor having low pressure drop
  Yosuke Ashikari; Kei Maekawa; Masahiro Takumi; Noriyuki Tomiyasu; Chiemi Fujita; Kiyoshi Matsuyama; Riichi Miyamoto; Hongzhi Bai; Aiichiro Nagaki
  Catalysis Today, 388-389, 231, 236, Elsevier BV, Apr. 2022, [Peer-reviewed], [Invited], [Lead author]
  Scientific journal
• Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization
  Yosuke Ashikari, Takashi Tamaki, Yusuke Takahashi, Yiyue Yao, Mahito Atobe, Aiichiro Nagaki
  Frontiers in Chemical Engineering, 3, 819752, Frontiers Media SA, Jan. 2022, [Peer-reviewed], [Invited], [Lead author]
  English, Scientific journal, Owing to its applicability in sustainable engineering, flow electrochemical synthesis in a proton-exchange membrane (PEM) reactor has attracted considerable attention. Because the reactions in PEM reactors are performed under electro-organic and flow-synthetic conditions, a higher number of reaction parameters exist compared to ordinary reactions. Thus, the optimization of such reactions requires significant amounts of energy, time, chemical and human resources. Herein, we show that the optimization of alkyne semihydrogenation in PEM reactors can be facilitated by means of Bayesian optimization, an applied mathematics strategy. Applying the optimized conditions, we also demonstrate the generation of a deuterated Z-alkene.
• フローマイクロケミストリーに基づく反応集積化
  永木愛一郎; 芦刈洋祐
  ケミカルタイムス, Jan. 2022, [Peer-reviewed], [Invited]
• Stille, Heck, and Sonogashira coupling and hydrogenation catalyzed by porous-silica-gel-supported palladium in batch and flow
  Yosuke Ashikari; Kei Maekawa; Mai Ishibashi; Chiemi Fujita; Kiyonari Shiosaki; Hongzhi Bai; Kiyoshi Matsuyama; Aiichiro Nagaki
  Green Processing and Synthesis, 10, 1, 722, 728, 18 Nov. 2021, [Peer-reviewed], [Lead author]
  English, Scientific journal
• フロー高速合成とAI活用の将来展望について
  永木愛一郎; 芦刈洋祐; 宅見正浩
  化学工学, 85, 11, 611, 614, Oct. 2021, [Peer-reviewed], [Invited]
• Switchable Chemoselectivity of Reactive Intermediates Formation and Their Direct Use in a Flow Microreactor
  Yosuke Ashikari; Takashi Tamaki; Tomoko Kawaguchi; Mai Furusawa; Yuya Yonekura; Susumu Ishikawa; Yusuke Takahashi; Yoko Aizawa; Aiichiro Nagaki
  Chemistry – A European Journal, 27, 65, 16107, 16111, Wiley, 22 Sep. 2021, [Peer-reviewed], [Lead author]
  Scientific journal
• Alkyne-Tagged Dopamines as Versatile Analogue Probes for Dopaminergic System Analysis
  Mutsuo Nuriya; Yosuke Ashikari; Takanori Iino; Takuya Asai; Jingwen Shou; Keiko Karasawa; Kaho Nakamura; Yasuyuki Ozeki; Yukari Fujimoto; Masato Yasui
  Analytical Chemistry, 93, 27, 9345, 9355, 01 Jul. 2021, [Peer-reviewed], [Lead author], [International Magazine]
  English, Scientific journal, The dopaminergic system is essential for the function of the brain in health and disease. Therefore, detailed studies focused on unraveling the mechanisms involved in dopaminergic signaling are required. However, the lack of probes that mimic dopamine in living tissues, owing to the neurotransmitter's small size, has hampered analysis of the dopaminergic system. The current study aimed to overcome this limitation by developing alkyne-tagged dopamine compounds (ATDAs) that have a minimally invasive and uniquely identifiable alkyne group as a tag. ATDAs were established as chemically and functionally similar to dopamine and readily detectable by methods such as specific click chemistry and Raman scattering. The ATDAs developed here were verified as analogue probes that mimic dopamine in neurons and brain tissues, allowing the detailed characterization of dopamine dynamics. Therefore, ATDAs can act as safe and versatile tools with wide applicability in detailed studies of the dopaminergic system. Furthermore, our results suggest that the alkyne-tagging approach can also be applied to other small-sized neurotransmitters to facilitate characterization of their dynamics in the brain.
• Homogeneous Catalyzed Aryl–Aryl Crosscouplings in Flow
  Yosuke Ashikari; Aiichiro Nagaki
  Synthesis, 53, 11, 1879, 1888, 18 Jan. 2021, [Peer-reviewed], [Invited], [Lead author]
  English, Scientific journal
• Multiple Organolithium Reactions for Drug Discovery Using Flash Chemistry
  Yosuke Ashikari; Takashi Tamaki; Masahiro Takumi; Aiichiro Nagaki
  Topics in Medicinal Chemistry, Springer Berlin Heidelberg, 2021, [Peer-reviewed], [Invited], [Lead author]
  In book
• Flash Chemistry Makes Impossible Organolithium Chemistry Possible
  Aiichiro Nagaki; Yosuke Ashikari; Masahiro Takumi; Takashi Tamaki
  Chemistry Letters, 50, 3, 485, 492, 17 Dec. 2020, [Peer-reviewed], [Invited]
  English, Scientific journal
• Accelerating Heat-Initiated Radical Reactions of Organic Halides with Tin Hydride Using Flow Microreactor Technologies
  Yiyuan Jiang; Yosuke Ashikari; Kaiteng Guan; Aiichiro Nagaki
  SYNLETT, 31, 19, 1937, 1941, Oct. 2020, [Peer-reviewed]
  English, Scientific journal
• A Synthetic Approach to Dimetallated Arenes Using Flow Microreactors and the Switchable Application to Chemoselective Cross-Coupling Reactions
  Yosuke Ashikari; Tomoko Kawaguchi; Kyoko Mandai; Yoko Aizawa; Aiichiro Nagaki
  Journal of the American Chemical Society, 142, 40, 17039, 17047, American Chemical Society (ACS), 28 Aug. 2020, [Peer-reviewed], [Lead author]
  Scientific journal
• Synthesis of Biaryls Having a Piperidylmethyl Group Based on Space Integration of Lithiation, Borylation, and Suzuki-Miyaura Coupling
  Yusuke Takahashi; Yosuke Ashikari; Masahiro Takumi; Yutaka Shimizu; Yiyuan Jiang; Ryosuke Higuma; Susumu Ishikawa; Hodaka Sakaue; Ibuki Shite; Kei Maekawa; Yoko Aizawa; Hiroki Yamashita; Yuya Yonekura; Marco Colella; Renzo Luisi; Toshihiro Takegawa; Chiemi Fujita; Aiichiro Nagaki
  EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 5, 618, 622, Feb. 2020, [Peer-reviewed]
  English, Scientific journal
• A Novel Approach to Functionalization of Aryl Azides through the Generation and Reaction of Organolithium Species Bearing Masked Azides in Flow Microreactors
  Daisuke Ichinari; Yosuke Ashikari; Kyoko Mandai; Yoko Aizawa; Jun-ichi Yoshida; Aiichiro Nagaki
  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 59, 4, 1567, 1571, Jan. 2020, [Peer-reviewed]
  English, Scientific journal
• O-18-Labeled chiral compounds enable the facile determination of enantioselectivity by mass spectroscopy
  Kyoko Mandai; Yuta Tsuchihashi; Yousuke Ashikari; Jun-ichi Yoshida; Aiichiro Nagaki
  TETRAHEDRON LETTERS, 61, 2, Jan. 2020, [Peer-reviewed]
  English, Scientific journal
• Pd catalysts supported on dual-pore monolithic silica beads for chemoselective hydrogenation under batch and flow reaction conditions
  Tsuyoshi Yamada; Aya Ogawa; Hayato Masuda; Wataru Teranishi; Akiko Fujii; Kwihwan Park; Yosuke Ashikari; Noriyuki Tomiyasu; Tomohiro Ichikawa; Riichi Miyamoto; Hongzhi Bai; Kiyoshi Matsuyama; Aiichiro Nagaki; Hironao Sajiki
  Catalysis Science & Technology, 10, 18, 6359, 6367, Royal Society of Chemistry (RSC), 2020, [Peer-reviewed]
  Scientific journal,

  Two different types of palladium catalysts supported on dual-pore monolithic silica beads [5% Pd/SM and 0.25% Pd/SM(sc)] for chemoselective hydrogenation were developed.

• Oxo-Thiolation of Cationically Polymerizable Alkenes Using Flow Microreactors
  Yosuke Ashikari; Kodai Saito; Toshiki Nokami; Jun-ichi Yoshida; Aiichiro Nagaki
  CHEMISTRY-A EUROPEAN JOURNAL, 25, 67, 15239, 15243, Dec. 2019, [Peer-reviewed]
  English, Scientific journal
• Development of Alkyne-tagged Dopamines: Molecular Probe for Dopamine Imaging using Click Chemistry
  Yosuke Ashikari; Yukari Fujimoto; Masato Yasui; Mutsuo Nuriya
  Proceedings for Annual Meeting of The Japanese Pharmacological Society, 92, 0, 3, O, Japanese Pharmacological Society, 2019, [Peer-reviewed], [Lead author]
  Scientific journal
• Metal-Free Benzylic C-H Amination via Electrochemically Generated Benzylaminosulfonium Ions
  Ryutaro Hayashi; Akihiro Shimizu; Yetao Song; Yosuke Ashikari; Toshiki Nokami; Jun-ichi Yoshida
  CHEMISTRY-A EUROPEAN JOURNAL, 23, 1, 61, 64, Jan. 2017, [Peer-reviewed]
  English, Scientific journal
• Photoredox mediators for metal-free ring-opening metathesis polymerization
  Laura Murphy; Damian Dunford; Adam Goetz; Kelli Ogawa; Yosuke Ashikari; Andrew Boydston
  ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 252, Aug. 2016, [Peer-reviewed]
  English
• Reaction Integration Using Electrogenerated Cationic Intermediates
  Jun-ichi Yoshida; Akihiro Shimizu; Yosuke Ashikari; Tatsuya Morofuji; Ryutaro Hayashi; Toshiki Nokami; Aiichiro Nagaki
  BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 88, 6, 763, 775, Jun. 2015, [Peer-reviewed]
  English
• Switching the reaction pathways of electrochemically generated beta-haloalkoxysulfonium ions - synthesis of halohydrins and epoxides
  Akihiro Shimizu; Ryutaro Hayashi; Yosuke Ashikari; Toshiki Nokami; Jun-ichi Yoshida
  BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 11, Feb. 2015, [Peer-reviewed]
  English, Scientific journal
• Addition of N-Acyliminium Ion Pools to Alkenes Having a Nucleophilic Moiety: Integration of Intermolecular and Intramolecular Reactions
  Yosuke Ashikari; Yohei Kiuchi; Tomoya Takeuchi; Koji Ueoka; Seiji Suga; Jun-ichi Yoshida
  CHEMISTRY LETTERS, 43, 2, 210, 212, Feb. 2014, [Peer-reviewed]
  English, Scientific journal
• Recent Developments in the "Cation Pool" Method
  Jun-ichi Yoshida; Yosuke Ashikari; Kouichi Matsumoto; Toshiki Nokami
  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 71, 11, 1136, 1144, Nov. 2013, [Peer-reviewed]
  English, Scientific journal
• Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization
  Yosuke Ashikari; Akihiro Shimizu; Toshiki Nokami; Jun-ichi Yoshida
  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 135, 43, 16070, 16073, Oct. 2013, [Peer-reviewed]
  English, Scientific journal
• The Addition of ArSSAr to Alkenes: The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)(+)
  Kouichi Matsumoto; Tomonari Sanada; Hayato Shimazaki; Kazuaki Shimada; Shino Hagiwara; Shunsuke Fujie; Yosuke Ashikari; Seiji Suga; Shigenori Kashimura; Jun-ichi Yoshida
  ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2, 4, 325, 329, Apr. 2013, [Peer-reviewed]
  English, Scientific journal
• Reaction Integration Using Electrochemically Generated Cationic Species
  Yosuke Ashikari
  Kyoto University, 2013, [Peer-reviewed]
  English, Doctoral thesis
• Integration of electrooxidative cyclization and chemical oxidation via alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization
  Yosuke Ashikari; Toshiki Nokami; Jun-ichi Yoshida
  ORGANIC & BIOMOLECULAR CHEMISTRY, 11, 20, 3322, 3331, 2013, [Peer-reviewed]
  English, Scientific journal
• Electrophilic substitution reactions using an electrogenerated ArS(ArSSAr)(+) cation pool as an ArS+ equivalent
  Kouichi Matsumoto; Yuki Kozuki; Yosuke Ashikari; Seiji Suga; Shigenori Kashimura; Jun-ichi Yoshida
  TETRAHEDRON LETTERS, 53, 15, 1916, 1919, Apr. 2012, [Peer-reviewed]
  English, Scientific journal
• Oxidative Hydroxylation Mediated by Alkoxysulfonium Ions
  Yosuke Ashikari; Toshiki Nokami; Jun-ichi Yoshida
  ORGANIC LETTERS, 14, 3, 938, 941, Feb. 2012, [Peer-reviewed]
  English, Scientific journal
• Integrated Electrochemical-Chemical Oxidation Mediated by Alkoxysulfonium Ions
  Yosuke Ashikari; Toshiki Nokami; Jun-ichi Yoshida
  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 133, 31, 11840, 11843, Aug. 2011, [Peer-reviewed]
  English, Scientific journal
• Electro-initiated Coupling Reactions of N-Acyliminium Ion Pools with Arylthiomethylsilanes and Aryloxymethylsilanes
  Seiji Suga; Ikuo Shimizu; Yosuke Ashikari; Yusuke Mizuno; Tomokazu Maruyama; Jun-ichi Yoshida
  CHEMISTRY LETTERS, 37, 9, 1008, 1009, Sep. 2008, [Peer-reviewed]
  English, Scientific journal

• University of Washington での研究生活
  芦刈洋祐, OMNews, 2023, 3, 102, 103, Aug. 2023, [Invited], [Lead author, Last author, Corresponding author]
  Japanese, Introduction other
• 二階層構造シリカモノリス担持型パラジウム触媒による官能基選択的接触水素化反応
  藤井明子; 山田強; 小川綾; 増田快音; 寺西航; 朴貴煥; 芦刈洋祐; 富安範行; 市川智大; 宮本利一; 白鴻志; 松山清; 松山清; 永木愛一郎; 佐治木弘尚, 日本病院薬剤師会東海ブロック・日本薬学会東海支部合同学術大会講演要旨集, 2020, 2020

• ベイズ最適化の活用事例 材料探索／物性予測／配合・プロセス条件の最適化
  芦刈洋祐; 永木愛一郎, フロー合成におけるベイズ最適化の活用と自動合成（第6章4節）
  技術情報協会, Mar. 2025, 9784867980668, [Contributor]
• ファインケミカル, 医薬品の連続生産プロセス
  技術情報協会, フロー合成における自動化・ロボット化技術とその活用法（第1章6節）
  技術情報協会, Nov. 2024, 9784867980514, 610p, Japanese, [Contributor]
• リビング重合技術 高度な制御を可能にする精密重合と応用展開
  早乙女広樹; 芦刈洋祐; 永木愛一郎, リビング重合の制御性向上に寄与するフローマイクロリアクターシステム
  Oct. 2024, 9784864283229, [Contributor]
• 月刊ファインケミカル2024年7月号「フロー・マイクロ合成―次世代合成の最前線―」
  芦刈洋祐; 永木愛一郎, AIを活用したフロー化学研究
  Jul. 2024, [Contributor]
• 実験の自動化・自律化によるR&Dの効率化と運用方法
  芦刈洋祐; 玉木孝; 永木愛一郎, AI技術を用いたフロー自動合成と実験の短縮
  技術情報協会, Dec. 2023, 9784861049941, [Contributor]
• Enabling Tools and Techniques for Organic Synthesis: A Practical Guide to Experimentation, Automation, and Computation
  Yosuke Ashikari; Aiichiro Nagaki, Introduction to Flow Chemistry for the Synthetic Chemist
  Willy, Oct. 2023, 9781119855637, [Contributor]
• フローマイクロ合成の最新動向
  芦刈洋祐; 永木愛一郎, 高分子合成反応
  シーエムシー出版, Aug. 2021, [Contributor]
• マイクロ・ナノ熱工学の進展
  芦刈洋祐、永木愛一郎, マイクロチャネル：マイクロ混合・反応
  マイクロ・ナノ熱工学の進展編集委員会, May 2021, 9784860437220, 6, 10, 731, 17p, 図版 [38] p, Japanese, [Contributor]
• フロー合成、連続生産のプロセス設計、条件設定と応用事例
  前川圭; 芦刈洋祐; 永木愛一郎, フローリアクターを用いた鈴木－宮浦カップリング反応
  技術情報協会, Dec. 2020, [Contributor]
• フロー合成、連続生産のプロセス設計、条件設定と応用事例
  芦刈洋祐; 永木愛一郎, フローリアクターを用いた不安定中間体を経由する反応集積化
  技術情報協会, Dec. 2020, [Contributor]
• フロー合成、連続生産のプロセス設計、条件設定と応用事例
  芦刈洋祐; 永木愛一郎, フローマイクロリアクターの高速混合を利用した高選択的化学反応
  技術情報協会, Dec. 2020, [Contributor]
• マイクロリアクター/フロー合成による 反応条件を最適化した導入と目的に応じた実生産への適用 ～事例をふまえた現状と課題 / 不具合を避けるための設備設計～
  芦刈 洋祐; 永木 愛一郎, 有機合成への応用技術と実用化事例
  サイエンス＆テクノロジー, 28 Apr. 2020, [Contributor]

• Flow Microreactor-Based Selectivity Control of Electrochemical Reactions
  Yosuke Ashikari
  The 105th CSJ Annual Meeting, Asian International Symposium, Mar. 2025, English, Invited oral presentation
  [Invited]
• フローマイクロ合成化学に立脚した高反応性化学種の自在制御法の開拓
  芦刈洋祐
  日本化学会北海道支部奨励賞受賞講演会, Feb. 2025, Japanese
  [Invited]
• In-Line Analysis of Reactive Intermediates in Flow Microreactors:A Flash Monitoring Strategy (poster)
  Yosuke Ashikari; Rikako Yoshioka; Yuya Yonekura; Dong-eun Yoo; Kazuhiro Okamoto; Aiichiro Nagaki
  The 17th International Conference on Cutting Edge Organic Chemistry in Asia (ICCEOCA2024), Nov. 2024, English, Poster presentation
  [Invited]
• Regioselective Electrocatalytic Deuteration Reactions in PEM Reactor
  Yosuke Ashikari; Yiyue Yao; Masahiro Takumi; Aiichiro Nagaki
  Pacific Rim Meeting on Electrochemical and Solid State Science 2024 (PRiME2024), 05 Oct. 2024, Oral presentation
• Flowmicro anionic polymerization driven by Flash Monitoring Approach, an in-line analysis method
  Yosuke Ashikari; Rikako Yoshioka; Yuya Yonekura; Dong-eun Yoo; Kazuhiro Okamoto; Aiichiro Nagaki
  International Conferences on Microreaction Technology 17 (IMRET17), Oct. 2024, English, Oral presentation
• 重合活性種のインライン分析に基づくメタクリレート類のフローマイクロアニオン重合
  芦刈洋祐; 吉岡里佳子; 米倉裕哉; 劉東垠; 岡本和紘; 永木愛一郎
  第73回高分子討論会, 25 Sep. 2024, Oral presentation
• 高反応性化学種の自在制御を志向したフローマイクロ合成化学
  芦刈洋祐
  鳥取大学講演会, 05 Sep. 2024, Public discourse
  [Invited]
• 高速フロー電解セルを用いたO-Cグリコシド転位反応の開発
  芦刈洋祐; 姚弋越; 宅見正浩; 永木愛一郎
  第48回有機電子移動化学討論会, 21 Jun. 2024, Oral presentation
• 高速電解フロー法を基軸とするO-Cグリコシド転位反応の速度研究および合成応用
  姚弋越; 芦刈洋祐; 宅見正浩; 永木愛一郎
  日本化学会第104年会, 20 Mar. 2024, Oral presentation
• Flash Synthetic Chemistry Guided by Flow Microreactor Research
  Yosuke Ashikari
  3rd International Conference on Automated Flow and Microreactor Synthesis (ICAMS-3), Dec. 2023, Invited oral presentation
  [Invited]
• フローマイクロリアクターを活用した高速反応制御およびデータ駆動型研究開発
  芦刈洋祐
  第101回フロー・マイクロ合成研究会, Nov. 2023, Invited oral presentation
  [Invited]
• プロトン交換膜型電解リアクターを用いた重水素導入法の開発と機械学習による条件最適化
  芦刈洋祐; 姚弋越; 萬代恭子; 玉木孝; 永木愛一郎
  第47回有機電子移動化学討論会, Jun. 2023, Poster presentation
• フローマイクロリアクターを用いたバイメタリックアレーンの合成と非対称ビアリール合成への展開
  芦刈洋祐; 川口倫子; 永木愛一郎
  日本農芸化学会2023年度大会, 16 Mar. 2023, Japanese, Poster presentation
• 高速マイクロ混合に基づくタンパク質の水中化学修飾の研究
  芦刈洋祐
  公益財団法人中外創薬科学財団令和4年度助成研究報告会, 03 Mar. 2023, Japanese, Poster presentation
  40291454, [Invited]
• アニオン重合の実用化を志向したフロー精密重合の実証
  芦刈洋祐
  HSFC Demo Day, 28 Feb. 2023, Japanese, Invited oral presentation
  40291463, [Invited]
• アニオン性マスク法に基づくバイメタリックアレーンのフローマイクロ合成
  芦刈洋祐; 永木愛一郎
  化学系学協会北海道支部2023年冬季研究発表会, 24 Jan. 2023, Japanese, Oral presentation
• フローマイクロリアクターにより合成したバイメタリックアレーン類の化学選択的カップリング反応
  芦刈洋祐; 川口倫子; 萬代恭子; 相澤瑤子; 永木愛一郎
  日本化学会第101春季年会, 21 Mar. 2021, Japanese, Oral presentation
• Generation and Reactions of Aryllithiums via Highly-Coordinated Anionic Intermediates Using Flow Microreactors
  Yosuke ASHIKARI; Daisuke ICHINARI; Kyoko MANDAI; Yoko AIZAWA; Jun-ichi YOSHIDA; Aiichiro NAGAKI
  日本化学会第100春季年会, Mar. 2020, English, Oral presentation
• 電解発生有機硫黄カチオン種を利用した重合性アルケンのオキソチオレーション
  芦刈洋祐; 齊藤巧泰; 野上敏材; 吉田潤一; 永木愛一郎
  日本化学会第100春季年会, Mar. 2020, Japanese, Oral presentation
• Masked Azide Strategy: Functionalization of Organic Azides via Generation and Reactions of Organolithiums using Flow Microreactors
  Yosuke Ashikari; Daisuke Ichinari; Yoko Aizawa; Kyoko Mandai; Jun-ichi Yoshida; Aiichiro Nagaki
  The 18th Asian Chemical Congress (18ACC), Dec. 2019, English
  08 Dec. 2019 - 12 Dec. 2019, [Invited]
• Oxo-thiolation of Cationically Polymerizable Alkenes with Anodic Cations Using Flow Microreactors
  Yosuke Ashikari; Kodai Saito; Toshiki Nokami; Jun-ichi Yoshida; Aiichiro Nagaki
  The 12th International Symposium on Integrated Synthesis (ISONIS-12), Nov. 2019, English, Poster presentation
  21 Nov. 2019 - 23 Nov. 2019

• Nov. 2024 - Present
  近畿化学協会
• Apr. 2024 - Present
  高分子学会
• Nov. 2023 - Present
  電気化学会
• 2023 - Present
  日本農芸化学会
• 2011 - Present
  THE SOCIETY OF SYNTHETIC ORGANIC CHEMISTRY
• 2008 - Present
  THE CHEMICAL SOCIETY OF JAPAN

• 高速フロー法を活用したカルボカチオンの性質解明に立脚したグリコシル化反応の開発
  科学研究費助成事業
  01 Apr. 2024 - 31 Mar. 2027
  芦刈 洋祐
  日本学術振興会, 基盤研究(C), 北海道大学, 24K08421
• 糖化学の新展開のための非平衡カルボカチオン化学のネットワーク構築
  科学研究費助成事業 国際共同研究加速基金(国際共同研究強化(B))
  27 Oct. 2020 - 31 Mar. 2026
  永木 愛一郎; 宮村 浩之; 信田 尚毅; 殿村 修; 芦刈 洋祐
  有機カチオン種は正電荷を有した短寿命な活性中間体であり、化学反応や生体反応において最も頻繁に発生する中間体の一つである。有機化学分野で古くから合成に利用されており、現在も主にカチオン前駆体とLewis酸から求核剤が共存する条件においてカチオン中間体を平衡的（可逆的）に発生させ、求核剤で瞬時に補足することにより様々な化合物合成に利用されている。一方で、有機カチオン種は、その不安定さから求核剤の共存しない条件（非共存条件）において非平衡的（不可逆的）に発生させることは困難であり、これがカチオン化学の展開を妨げてきた。特に糖鎖合成の中心となるグリコシル化反応の鍵中間体と考えられているグリコシルカチオンは、極めて不安定であることから、直接的な観測は達成されておらず、その構造や反応性の研究は推定の域を出ていない。このような背景のもと、本国際共同研究では、フランスポワティエ大学のThibaudeau教授との共同研究を通し、我々のフローマイクロ合成技術とThibaudearu教授の超強酸技術とを融合させた超強酸フロー技術の構築を行う。本年度は、フローマイクロリアクターを用いた不可逆的なグリコシルカチオン発生を目指し、高速電解合成が可能なフロー型電解合成装置の開発を行った。その結果、グリコシルカチオンと同種の構造を有する環状オキソニウムカチオンの発生と反応をフロー反応により達成できた。次年度は本装置を活用し、グリコシルカチオンのフローリアクターによる発生に挑戦したい。
  日本学術振興会, 国際共同研究加速基金(国際共同研究強化(B)), 京都大学, 20KK0121
• フローマイクロ技術による生体高分子の高精度ケミカルコンジュゲーションの研究
  令和6年度研究助成金援助事業
  Apr. 2024 - Mar. 2026
  公益財団法人高橋産業経済研究財団, Principal investigator
• 不安定カチオン種の発生・反応および分析を可能とする電気化学反応装置の開発研究補助事業
  2024年度自転車等機械振興事業に関する補助金
  Apr. 2024 - Mar. 2026
  公益財団法人JKA, Principal investigator, 2024M-521
• 高度に構造の制御された人工高分子材料の生産事業に向けた検討
  大学発新産業創出基金事業スタートアップ・エコシステム共創プログラム
  Oct. 2024 - Sep. 2025
  北海道 未来創造スタートアップ育成相互支援ネットワーク, Principal investigator
• 重水素化機能材料の創生を志向した電解フローリアクターの開発
  2023年度自転車等機械振興事業に関する補助金
  Apr. 2023 - Mar. 2024
  芦刈洋祐
  公益財団法人JKA, Principal investigator, 2023M-326
• 高速マイクロ混合に基づくタンパク質の水中化学修飾の研究
  研究奨励金B-I
  Apr. 2022 - Mar. 2023
  芦刈洋祐
  公益財団法人中外創薬科学財団, 北海道大学, Principal investigator
• Advanced utilization of multiple short-lived reactive species by application of flash flow electrolysis
  Grants-in-Aid for Scientific Research Grant-in-Aid for Early-Career Scientists
  Apr. 2020 - Mar. 2023
  芦刈 洋祐
  不安定活性種を不可逆的に発生可能な有機電解反応において、従来不可能であった、炭素カチオンなどの不安定活性種の合成利用を実現すべく研究を行った。特に寿命が1秒に満たないような極めて不安定な炭素カチオンなどの活性種を短時間で発生できるフローマイクロ電解装置を開発し、その高次利用を基軸とした、複数の活性種を経由する新規分子変換反応の開発を目指して研究を行った。本年度は、昨年度に引き続き電極の材質を最適化するとともに、電解反応デバイス自体の改良を行った。その結果、バッチ型電解装置ではほとんど生成物の得られない、オキソニウムカチオンの発生とその求核剤との反応を高効率的に行うことができた。さらにこれまで検討してきた小スケール合成に加えて、生産を志向した大スケール合成の検討を行った。すなわち不安定中間体の一種であるイミニウムカチオンの発生と反応において、長時間の送液が可能な送液装置を活用し、60分間の連続反応を行うことにより、生理活性物質の前駆体をグラムスケールで合成することに成功した。これは、装置および反応システムの頑健性を示すものであり、大スケール生産や合成の工業化に展開可能であることを示す結果である。今後は、極めて不安定でありながら合成価値の高い活性種であるグリコシルカチオンおよびその類縁体に注力し、その発生と合成利用を可能とするフローマイクロ電解装置および電解技術の開発とその実現に挑戦していく。
  Japan Society for the Promotion of Science, Grant-in-Aid for Early-Career Scientists, Kyoto University, Principal investigator, 20K15276
• アニオン重合の実用化を志向したフロー精密重合の実証
  大学発新産業創出プログラム(START) 大学・エコシステム推進型 起業活動支援プログラム研究開発課題
  Oct. 2022 - Feb. 2023
  芦刈洋祐
  公益財団法人北海道科学技術総合振興センター, 北海道大学, Principal investigator
• 多種金属置換基を有する芳香族化合物合成法の確立とそのカップリング反応の開拓
  2021年度研究開発助成
  Apr. 2021 - Mar. 2022
  芦刈洋祐
  京都技術科学センター, 京都大学大学院, Principal investigator
• 令和2年度国際研究集会発表助成
  Dec. 2020 - Dec. 2020
  芦刈洋祐
  公益財団法人京都大学教育研究振興財団
• Characterization of structure function relatioship of astrocyte
  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)
  01 Apr. 2016 - 31 Mar. 2019
  Nuriya Mutsuo; ASHIKARI Yosuke; MIZUGUCHI Takaha
  In this study, we investigated the structure-function relationship of astrocytes, non-neuronal cells whose roles in brain physiology and pathophysiology have been recently realized. We revealed that various proteins that were located at the microstructures of astrocytes were dynamically regulated by drugs and biological molecules that had been considered to exert their functions through their actions on neurons. Furthermore, we have also succeeded in developing and applying microscopy methods that are effective in investigating astrocyte functions. Future studies based on these progresses are expected to reveal the structure function relationship of astrocytes and its roles in physiology and pathophysiology of the brain.
  Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C), Keio University, 16K07065

• シークエンスオリゴマー及びポリマー並びにその製造方法
  Patent right, 永木 愛一郎; 芦刈 洋祐; 北山 健司, 国立大学法人京都大学, 株式会社ダイセル
  特願2022-075734, 02 May 2022
  特開2023-165103, 15 Nov. 2023
• 白金族元素担持多孔性粒子及び白金族元素触媒、並びにこれらが充填されたカラム
  Patent right, 永木 愛一郎; 前川 圭; 芦刈 洋祐; 石塚 紀生; 松山 清, 株式会社ａｌｔＦｌｏｗ, 株式会社エマオス京都
  特願2021-191997, 26 Nov. 2021
  特開2023-078733, 07 Jun. 2023
• ポリマーの製造方法、並びにハロゲン化スチレン類モノマー重合用開始剤、及びその製造方法
  Patent right, 永木愛一郎; 石川進; 高橋裕輔; 芦刈洋祐; 古澤真維; 米倉裕哉; 玉木孝, 国立大学法人京都大学, 東邦化学工業株式会社
  特願2021-032262, Mar. 2021
• モノ重水素化ジハロゲン化メタン、重水素化シクロプロパン化合物及びそれらの製造方法
  Patent right, 永木愛一郎; 芦刈洋祐; 土橋祐太, 国立大学法人京都大学, 大陽日酸株式会社
  特願2020-214198, 23 Dec. 2020
• Additive Manufacturing Using Stimuli-Responsive High-Performance Polymers
  Patent right, Lee. C.-U; Goetz, A. E; Ashikari, Y; Boydston, A. J; Ganter, M. A; Storti, D. W, リコー、ユニヴァーシティオブワイントン
  特願2018-036249, 01 Mar. 2018
  特開2018-144488, 20 Sep. 2018
• 化合物、化合物の塩、神経機能調節物質、神経機能調節物質の評価方法、化合物の製造方法、及び化合物の塩の製造方法
  Patent right, 塗谷睦生; 芦刈洋祐; 藤本ゆかり; 安井正人, 学校法人慶應義塾
  特願2020-535822, 07 Aug. 2018