Hikaru Yanai - My portal

Profile Information

Affiliation: Associate Professor, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences

Degree: Doctor of Philosophy(Tokyo University of Pharmacy and Life Science)

ORCID ID: https://orcid.org/0000-0003-4638-5113
researchmap Member ID: 5000092014

External link: https://tupls-matsumotoken.jimdofree.com/

有機フッ素化学を基盤に、『硫酸よりも強い有機酸』、『ねじれたエチレン』、『手に取ることのできるカルボアニオン』などの設計・合成を手がけてきました。最近は、珍しいπ共役系の合成と溶解・分配特性といった巨視的物性の制御に興味をもっています。独創的かつ有益な研究成果を目指して、フラスコを眺める日々です。

Research Interests

Research Areas

Research History

Apr, 2016 - Present

Associate Professor, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
Apr, 2013 - Present

Lecturer (part-time), Tokyo University of Agriculture and Technology
Sep, 2018 - Oct, 2018

Invited Professor, Université Caen-Normandie
Jul, 2014 - Mar, 2016

Senior Lecturer, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
Sep, 2008 - Jun, 2014

Assistant Professor, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
Oct, 2013 - Dec, 2013

Visiting Researcher, Université Claude Bernard Lyon 1-CNRS
Apr, 2005 - Jul, 2008

Research Assistant, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences

Education

Apr, 2002 - Mar, 2005

Graduate School of Pharmaceutical Sciences, Tokyo University of Pharmacy and Life Sciences
Apr, 1998 - Mar, 2002

Division of Pharmaceutical Sciences, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences

Committee Memberships

Aug, 2023 - Present

産学連携部会学界会員, 日本フッ素化学会
Aug, 2023 - Present

第40回有機合成化学セミナー実行委員, 有機合成化学協会
May, 2023 - Present

企画委員, 日本フッ素化学会
Mar, 2023 - Present

Editorial Board of J. Synth. Org. Chem., Jpn., The Society of Synthetic Organic Chemistry, Japan
2020 - Present

Editorial Board of "Fluorine", The Society of Fluorine Chemistry, Japan
2022 - 2023

第11回フッ素化学若手の会実行委員長, 日本フッ素化学会
2008 - 2015

次世代を担う有機化学シンポジウム世話人, 日本薬学会
2010 - 2011

第1回フッ素化学若手の会実行委員, 日本フッ素化学会
2009 - 2010

第3回日本薬学会関東支部若手シンポジウム実行委員, 日本薬学会

Awards

Papers

Phosphite-imidazole catalyzed N-formylation and N-acylation of amines

B. Kaboudin, H. Esfandiari, M. Kakavand, M. Sohrabi, E. Yousefian Amirkhiz, A. Nesha, T. Kawazoe, H. Fukaya, H. Yanai

Organic & Biomolecular Chemistry, 21(40) 8182-8189, Oct, 2023 Peer-reviewedCorresponding author
Diverse synthesis of 2H-isoindole-based polycyclic aromatic compounds

T. Kawazoe, H. Yanai, Y. Hagiyama, K. Funabiki, T. Matsumoto

Chemistry – A European Journal, 29(50) e202301703, Sep, 2023 Peer-reviewedCorresponding author
Development of stable carbanionic substituents

H. Yanai

The Chemical Record, 23(9) e202300076, Sep, 2023 Peer-reviewedInvitedLead authorCorresponding author
Stereoselective synthesis of vinylphosphonates through aromatic aza-Claisen rearrangement of α-aminophosphonates

B. Kaboudin, M. Ghashghaee, H. Fukaya, H. Yanai

Chemical Communications (Cambridge, United Kingdom), 59(46) 7076-7079, Jun, 2023 Peer-reviewedCorresponding author
Total synthesis of patulone, a natural xanthonoid possessing geminally diisoprenylated structure

R. Kobayashi, Y. Watabe, Y. Fujimoto, H. Yanai, T. Matsum

Synlett, 34(8) 953-957, Apr, 2023 Peer-reviewed
Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

H. Yanai, M. R. Márquez, S. Cembellín, T. Martínez del Campo, P. Almendros

Organic Chemistry Frontiers, 10(7) 1773-1779, Mar, 2023 Peer-reviewedLead author
Reversing the bond length alternation order in conjugated polyenes by substituent effects

H. Yanai, Y. Terajima, F. Kleemiss, S. Grabowsky, T. Matsumoto

Chemistry – A European Journal, 29(15) e202203538, Mar, 2023 Peer-reviewedLead authorCorresponding author
Au(I) as a π-Lewis base catalyst: Controlled synthesis of sterically congested bis(triflyl)enals from α-allenols

M. Toledano-Pinedo, T. Martínez del Campo, H. Yanai, P. Almendros

ACS Catalysis, 12(19) 11675-11681, Sep, 2022 Peer-reviewed
Synthesis of spirocyclic cyclobutenes through desulfinative spirocyclisation of gem-bis(triflyl)cyclobutenes

S. Hoshikawa, H. Yanai, T. Matsumoto

Chemistry – A European Journal, 28(33) e202200704, May, 2022 Peer-reviewedCorresponding author
ZnCl₂-mediated stereo- and chemoselective synthesis of vinylphosphonates

B. Kaboudin, A. Moradi, H. Esfandiari, P. Daliri, F. Kazemi, H. Yanai, H. Aoyama

Organic & Biomolecular Chemistry, 20(12) 2500-2507, Mar, 2022 Peer-reviewedCorresponding author
Chemistry of carbanions stabilised by (trifluoromethyl)sulfonyl group: Synthesis, structure and applications

H. Yanai

Yuki Gosei Kagaku Kyokaishi, 80(3) 186-197, Mar, 2022 Peer-reviewedInvitedCorresponding author
Synthesis of polycyclic aromatic hydrocarbons decorated by fluorinated carbon acids/carbanions

S. Hoshikawa, H. Yanai, I. Martín-Mejías, C. Lázaro-Milla, C. Aragoncillo, P. Almendros, T. Matsumoto

Chemistry – A European Journal, 27(65) 16112-16116, Nov, 2021 Peer-reviewedCorresponding author
Diaminomethylenemalononitrile as a chiral single hydrogen bond catalyst: Application to enantioselective conjugate addition of α-branched aldehydes

M. Kawada, R. Tsuyusaki, K. Nakashima, H. Akutsu, S. Hirashima, T. Matsumoto, H. Yanai, T. Miura

Chemistry – An Asian Journal, 16(16) 2272-2275, Aug, 2021 Peer-reviewedCorresponding author
Regioselective synthesis of 4-aryl-1,3-dihydroxy-2-naphthoates through 1,2-aryl-migrative ring rearrangement reaction and their photoluminescence properties

H. Yanai, T. Kawazoe, N. Ishii, B. Witulski, T. Matsumoto

Chemistry – A European Journal, 27(44) 11442-11449, Aug, 2021 Peer-reviewedLead authorCorresponding author
Metal-free C–C/C–N/C–C bond formation cascade for the synthesis of (trifluoromethyl)sulfonylated cyclopenta[b]indolines

C. Lázaro-Milla, H. Yanai, P. Almendros

Organic Letters, 23(8) 2921-2926, Apr, 2021 Peer-reviewed
pK_a Determination of strongly acidic C–H acids bearing a (perfluoroalkyl)sulfonyl group in acetonitrile by means of voltammetric reduction of quinone

A. Kotani, H. Yanai, T. Matsumoto, H. Hakamata

Electrochemistry, 89(2) 121-124, Mar, 2021 Peer-reviewedInvited
A fluorinated carbanionic substituent for improving water-solubility and lipophilicity of fluorescent dyes

H. Yanai, S. Hoshikawa, Y. Moriiwa, A. Shoji, A. Yanagida, T. Matsumoto

Angewandte Chemie International Edition, 60(10) 5168-5172, Mar, 2021 Peer-reviewedLead authorCorresponding author
S_NAr reaction/Claisen rearrangement approach to 2,4-diisoprenylxanthones: total synthesis of garcinone A

M. Mochizuki, Y. Fujimoto, H. Yanai, T. Matsumoto

Synlett, 31(15) 1511-1516, Sep, 2020 Peer-reviewed
Trifluorosulfonylation cascade in allenols: stereocontrolled synthesis of bis(triflyl)enones

C. Lázaro-Milla, J. Macicior, H. Yanai, P. Almendros

Chemistry – A European Journal, 26(41) 8983-8989, Jul, 2020 Peer-reviewed
Anion-accelerated aromatic oxy-Cope rearrangement in geranylation/nerylation of xanthone: stereochemical insights and synthesis of fuscaxanthone F

Y. Fujimoto, K. Takahashi, R. Kobayashi, H. Fukaya, H. Yanai, T. Matsumoto

Synlett, 31(14) 1378-1383, Apr, 2020 Peer-reviewed

Misc.

Hirshfeld Atom Refinement

H. Yanai

Yuki Gosei Kagaku Kyokaishi, 80(3) 281-281, Mar, 2022 InvitedCorresponding author
Development of novel synthetic reactions though specific properties of fluorine and fluorine-containing substituents

Hikaru Yanai

Chemical Industry, 70(8) 8-14, Aug, 2019 Invited
連続反応を活用した多置換多環式芳香族化合物の合成

矢内光

上原記念生命科学財団研究報告集, 32 108, Feb, 2018
Synthesis of carbanion-containing salts and their applications as novel organocatalysts

Yanai, H

Chemical Industry, 68(9) 73-78, Sep, 2017 Invited
Superacidic carbon acids: Synthesis and catalysis

Yanai, H

Fine Chemicals, 46(3) 21-28, Mar, 2017 Invited
超強酸性を示す炭素酸の基礎研究と有機分子触媒としての利用

矢内光

旭硝子財団助成研究成果報告, 1-5, Jan, 2015 Invited
フッ素導入による立体配座制御 : 有機分子触媒の新しい設計指針

矢内光

ファルマシア, 45(11) 1134-1135, Nov 1, 2009

Books and Other Publications

Green Synthetic Approaches for Biologically Relevant Heterocycles (Second Edition), Volume 2: Green Catalytic Systems and Solvents; G. Brahmachari (Ed.)

H. Yanai (Role: Contributor, Chapter 13. Green and catalytic methods for γ-lactone synthesis, pp. 537-615)

Elsevier, Mar, 2021 (ISBN: 9780128207925)
Development of Organocatalysts and Their Application to Industry; T. Akiyama (Ed.)

H. YANAI (Role: Contributor, Chapter 9. Molecular Transformations Mediated by Superacidic Carbon Acids, pp. 90–100)

CMC Publishing, Mar, 2018 (ISBN: 9784781313238)
フッ素化学入門2015

矢内光 (Role: Contributor, pp. 191-193, 220-223)

三共出版, Mar, 2015 (ISBN: 9784782707272)
Green Synthetic Approaches for Biologically Relevant Heterocycles; G. Brahmachari (Ed.)

H. Yanai (Role: Contributor, Chapter 10. Green and Catalytic Methods for γ-Lactone Synthesis, pp. 257-289)

Elsevier: Amsterdam, Nov, 2014 (ISBN: 9780128000700)
パートナー薬品製造学改訂第2版，野上靖純，田口武夫，長普子（編集）

田口武夫, 矢内光 (Role: Contributor, 第2章付加と脱離, pp. 63-91)

南江堂, Apr, 2012 (ISBN: 4524402942)
Fluorine in Medicinal Chemistry and Chemical Biology; I. Ojima (Ed)

T. Taguchi, H. Yanai (Role: Contributor, Chapter 10. Fluorinated Moieties for Replacement of Amide and Peptide Bonds, pp. 257-290)

Wiley-Blackwell: Chichester, 2009 (ISBN: 9781405167208)
Acid Catalysis in Modern Organic Synthesis, H. Yamamoto and K. Ishihara (Eds.)

T. Taguchi, H. Yanai (Role: Contributor, Chapter 6. Al(III) Lewis Acids, pp. 241-345.)

Wiley-VCH: Weinheim, 2008 (ISBN: 9783527317240)

Presentations

Controlling the solubility profiles of polycyclic aromatic compounds by carbanionic substituents

International Congress on Pure & Applied Chemistry (ICPAC) Bali 2023, Bali, Indonesia Invited
Fluorinated stable carbanions as substituents for controlling the solubility profiles of organic compounds

23rd International Symposium on Fluorine Chemistry, Québec City, Canada, Jul 27, 2023 Invited
HFIP-mediated detriflylative allylic substitution reactions on the cyclobutene platform

23rd International Symposium on Fluorine Chemistry, Québec City, Canada, Jul 24, 2023
The fluorine magic in drug discovery

Departmental seminar at Toyohashi University of Technology, Dec 6, 2022 Invited
Ring-rearrangement strategy for selective synthesis of pseudo aromatic polyketides

International Congress on Pure & Applied Chemistry (ICPAC), Kota Kinabalu, Malaysia, Nov 23, 2022 Invited
カルボアニオンで化合物を溶かす

日本フッ素化学会産学連携部会 10月講演会, Oct 21, 2022 Invited
Synthesis and applications of superacidic carbon acids

Seminar at Central Glass Co., Ltd., Mar 3, 2022 Invited
To draw, or not to draw: Chemistry of highly stablised carbanions and their applications

Departmental Seminar at Kumamoto University, Dec 8, 2020 Invited
To draw or not to draw: Chemistry of highly stabilized carbanions

Berner Chemische Gesellschaft, Oct 9, 2020 Invited
Fluorinated zwitterion-induced Mukaiyama aldol type reaction and its applications to naphthalene synthesis

19th European Symposium on Fluorine Chemistry, Warsaw, Poland, Aug 25, 2019
1,1-Bis(triflyl)ethylation reaction of heterocyclic compounds

19th European Symposium on Fluorine Chemistry, Warsaw, Poland, Aug 25, 2019
Elemental Chemistry of Carbon -Chemistry of superacidic carbon acids and their conjugate bases-

Departmental Seminar at Meiji Pharmaceutical University, Jan 22, 2019 Invited
線を描くべきか，描かざるべきかーフッ素で安定化されたカルボアニオンの化学ー

第7回フッ素化学研究講演会, Dec 5, 2018 Invited
From superacidic carbon acids to highyl stablised carbanions

Departmental Seminar at Université de Caen Normandie, Caen, France, Sep 14, 2018 Invited
Chemistry of carbanion-bearing zwitterions

Departmental Seminar at Faculté de Pharmacie, Université Paris-Sud, Chatenay-Malabry, France, Sep 13, 2018 Invited
Chemistry of highly stabilised carbanion -To draw, or not to draw-

Departmental Seminar at Université de Rouen Normandie, Mont Saint Aignan, France, Sep 7, 2018 Invited
Ultimately polarised push-pull ethylenes: unusual conformational behaviour and its application

The 22nd International Symposium on Fluorine Chemistry, Jul 22, 2018
Highly polarized push-pull ethylenes: synthesis, structure, and applications

26th French-Japanese Symposium on Medicinal and Fine Chemistry, Sep 17, 2017
Ultimate push-pull ethylenes from organofluorine Chemistry

The 8th International Meeting on Halogen Chemistry (HALCHEM VIII), Sep 14, 2017 Invited
Fluorine loves strong acid

Departmental Seminar at Tokyo University of Agriculture and Technology, Nov 16, 2016 Invited

Teaching Experience

Professional Memberships

Research Projects

Improvement of cell membrane permeability by fluorineted carbanion substitutents

Pharmaceutical Research Grants, Takeda Sciences Foundation, Sep, 2023 - Mar, 2026
Development of functional molecules bearing stable carbanion moieties

Grants-in-Aid for Scientific Research, Grants-in-Aid for Scientific Research (C), Japan Society of the Promotion of Science, Apr, 2023 - Mar, 2026
Development of novel cascade reactions for polysubstituted polycyclic aromatics

Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Japan Society for the Promotion of Science, Apr, 2020 - Mar, 2023
Development of novel fluorinated substituents deirected to medicinal chemistry

Invitational Fellowships for Research in Japan, Short-term, JSPS, Sep, 2022
蛍光色素の水溶性と脂溶性を制御する新手法の開発

知的財産創成研究費, 東京薬科大学, Apr, 2019 - Mar, 2020

矢内光
Structural chemistry on highly stabilized carbanions

Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Japan Society for the Promotion of Science, Apr, 2017 - Mar, 2020

Yanai Hikaru
強酸性炭素酸とその共役塩基に着目した新触媒の開発

研究助成, 公益財団法人篷庵社, Apr, 2015 - Mar, 2019

矢内光
連続反応を活用した多置換多環式芳香族化合物の合成

研究奨励金, 公益財団法人上原記念生命科学財団, Apr, 2017 - Mar, 2018

矢内光
高度に分極したアルケンの構造と反応性に立脚した触媒作用の探求

倉田奨励金, 公益財団法人倉田記念日立科学技術財団, Apr, 2015 - Mar, 2017

矢内光
Novel cascade reactions triggered by silyl acetal activation

Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Japan Society for the Promotion of Science, Apr, 2014 - Mar, 2017

Yanai Hikaru
Development of strongly acidic organocatalysts

Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research on Innovative Areas (Advanced Molecular Transformations by Organocatalysts), Ministry of Education, Culture, Sports, Science and Technology, Apr, 2014 - Mar, 2016

Hikaru Yanai
新しい酸性官能基の開発と触媒作用の探求

内藤記念特定研究助成金, 公益財団法人内藤記念科学振興財団, 2015 - 2016

矢内光
Development of novel acidic functionality directed to design of organocatalysts

Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research on Innovative Areas ( Advanced Molecular Transformations by Organocatalysts), Ministry of Education, Culture, Sports, Science and Technology, Apr, 2012 - Mar, 2014

Hikaru Yanai
Development of superacidic carbon acids: synthesis, characterization, and catalyst activity

Research Encouragement Grants, The Asahi Glass Foundation, Apr, 2012 - Mar, 2014

Hikaru Yanai
Development of new synthetic reactions based on novel acid catalysts

Grants-in-Aid for Scientific Research, Grant-in-Aid for Young Scientists (B), Japan Society for the Promotion of Science, 2010 - 2012

YANAI Hikaru
ビス（トリフルオロメチルスルホニル）メチル基を有する高活性酸触媒の開発

知的財産創成研究費, 東京薬科大学, Jan, 2011 - Dec, 2011

矢内光
Preparation of functionalized organofluorine compounds toward drug discovery

Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Japan Society for the Promotion of Science, 2008 - 2010

TAGUCHI Takeo, YANAI Hikaru
Development of functional molecules on the basis of design of novel Lewis acid catalysts

Grants-in-Aid for Scientific Research, Grant-in-Aid for Young Scientists (B), Japan Society for the Promotion of Science, 2007 - 2009

YANAI Hikaru
Development of synthetic methodogies for organofluorine compounds in medicinal chemistry

Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Japan Society for the Promotion of Science, 2005 - 2007

TAGUCHI Takeo, KITAGAWA Osamu, YANAI Hikaru

Industrial Property Rights

特許6333578 光学活性なフルオロアルケン誘導体およびその製造方法

矢内光, 松本隆司
特許5998948 Preparation of bis(trifluoromethylsulfonyl)methyl compounds and their use as acid catalysts

H. Yanai
特許5696465 Preparation of bis(trifluoromethanesulfonyl)ethyl-bearing phenolic compounds as acid catalysts, and method for preparing same

T. Taguchi, H. Yanai
特許5363010 Preparation of α-aminodifluoromethylene compounds

H. Yanai, T. Taguchi
特許4869739 Preparation of fluorine-containing quinolines from 2-vinylanilines via fluorine-containing dihydroquinolines

H. Yanai, T. Taguchi