Takahiko Akiyama

(秋山隆彦)

Profile Information

Affiliation: Faculty of Science, Department of Chemistry, Gakushuin University

ORCID ID: https://orcid.org/0000-0003-4709-4107
J-GLOBAL ID: 200901007447424579
researchmap Member ID: 1000167339

External link: https://www-cc.gakushuin.ac.jp/~940020/index_E.html

Research Interests

Research Areas

Research History

Apr, 1997 - Present

Professor, Department of Chemistry, Faculty of Science, Gakushuin University
Apr, 1994 - Mar, 1997

Associate Professor, Department of Chemistry, Gakushuin University
Jul, 1988 - Mar, 1994

Assistant Professor, Department of Resources Chemistry, Faculty of Engineering, Ehime University
Apr, 1992 - Mar, 1993

Visiting Scholar, Department of Chemistry, Stanford University
Apr, 1985 - Jun, 1988

Research Chemist, Shionogi Research Laboratories, Shionogi & Co., Ltd.

Education

- 1985

The University of Tokyo
- 1985

Graduate School, Division of Science, The University of Tokyo
- 1980

Department of Chemistry, Faculty of Science, The University of Tokyo
- 1980

Faculty of Science, The University of Tokyo

Committee Memberships

Feb, 2021 - Feb, 2023

会長, 有機合成化学協会
Apr, 2018 - Mar, 2022

学術システム研究センター主任研究員, 独立行政法人日本学術振興会
May, 2018 - May, 2020

理事, 日本化学会

Awards

Feb, 2018

Synthetic Organic Chemistry Award, Japan, The Society of Synthetic Organic Chemistry, Japan

AKIYAMA Takahiko
Aug, 2016

Arthur C. Cope Scholar Award, American Chemical Society

AKIYAMA Takahiko
Mar, 2016

Humboldt Research Award, Humboldt Foundation

AKIYAMA Takahiko
Nov, 2012

Nagoya Silver Medal, Banyu Life Science Foundation International

AKIYAMA Takahiko
Mar, 2009

The Chemical Society of Japan Award for Creative Work for 2009, The Chemical Society of Japan

Papers

Fluoride‐Coupled Electron Transfer and Hydrogen‐Atom‐Transfer‐Mediated Synthesis of Difluoromethylarenes

Tatsuhiro Uchikura, Kaho Ohashi, Fua Akutsu, Takahiko Akiyama

European Journal of Organic Chemistry, Dec 19, 2025
Transfer Hydrogenation of β-Trifluoromethylated Nitroalkenes Catalyzed by Chiral Calcium Phosphate

Tatsuhiro Uchikura, Yuki Kaneko, Takanobu Setogawa, Tatsushi Oishi, Takahiko Akiyama

ACS Organic & Inorganic Au, Aug 6, 2025
Visible-Light-Driven Racemization of 1,1′-Binaphthyl-2,2′-diamine (BINAM) Derivatives

Tatsuhiro Uchikura, Mikoto Sato, Yuki Kanno, Yukino Fukuda, Yurina Hara, Kota Yamamoto, Takahiko Akiyama

Organic Letters, Feb 28, 2025
Electron donor–acceptor (EDA) complex mediated visible-light driven sulfur–fluorine bond reduction of pentafluorosulfanyl arenes using potassium iodide

Tatsuhiro Uchikura, Fua Akutsu, Takahiko Akiyama

Chemical Communications, 2025
Synthesis of indole-fused benzodiazepine derivatives by photocatalyzed cascade reaction

Tatsushi Oishi, Tatsuhiro Uchikura, Takahiko Akiyama

Chemical Communications, 2025

Misc.

203

Asymmetric Reduction of Trifluoromethyl Alkynyl Ketimines by Chiral Phosphoric Acid and Benzothiazoline

Takahiko Akiyama, Masamichi Miyagawa, Kensuke Takashima

Synlett, Jul 16, 2018
Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp3)–H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process

Keiji Mori, Ryo Isogai, Yuto Kamei, Masahiro Yamanaka, Takahiko Akiyama

Journal of the American Chemical Society, 140(20) 6203-6207, May 23, 2018
Tishchenko reaction using substoichiometric amount of metallic zinc

Masamichi Miyagawa, Takahiko Akiyama

Chemistry Letters, 47(1) 78-81, 2018
Enantioselective Transfer Hydrogenation Reaction by Means of Chiral Bronsted Acid

46(3) 6-11, Mar, 2017
Highly Efficient Kinetic Resolution of PHANOL by Chiral Phosphoric Acid Catalyzed Asymmetric Acylation

Keiji Mori, Hiroki Kishi, Takahiko Akiyama

SYNTHESIS-STUTTGART, 49(2) 365-370, Jan, 2017
Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid

Kosaku Horiguchi, Eri Yamamoto, Kodai Saito, Masahiro Yamanaka, Takahiko Akiyama

CHEMISTRY-A EUROPEAN JOURNAL, 22(24) 8078-8083, Jun, 2016
Cluster Preface: BINOL Phosphates for Chemistry

Akiyama, T.

Synlett, 27(4) 542-545, Mar, 2016
Chiral Phosphoric Acid Catalyzed Kinetic Resolution of Indolines Based on a Self-Redox Reaction

Saito, K., Akiyama, T.

Angewandte Chemie - International Edition, 55(9) 3148-3152, Feb, 2016
Transformation of Trifluorotoluenes Triggered by Titanium(IV) Chloride-Catalyzed Hydrodefluorination using Hydrosilanes

Takayuki Yamada, Kodai Saito, Takahiko Akiyama

ADVANCED SYNTHESIS & CATALYSIS, 358(1) 62-66, Jan, 2016
Remarkable Differences in Reactivity between Benzothiazoline and Hantzsch Ester as a Hydrogen Donor in Chiral Phosphoric Acid Catalyzed Asymmetric Reductive Amination of Ketones

Kyung-Hee Kim, Takahiko Akiyama, Cheol-Hong Cheon

CHEMISTRY-AN ASIAN JOURNAL, 11(2) 274-279, Jan, 2016
Remarkable Differences in Reactivity between Benzothiazoline and Hantzsch Ester as a Hydrogen Donor in Chiral Phosphoric Acid Catalyzed Asymmetric Reductive Amination of Ketones

Kyung-Hee Kim, Takahiko Akiyama, Cheol-Hong Cheon

CHEMISTRY-AN ASIAN JOURNAL, 11(2) 274-279, Jan, 2016
Stronger Bronsted Acids: Recent Progress

Takahiko Akiyama, Keiji Mori

CHEMICAL REVIEWS, 115(17) 9277-9306, Sep, 2015
B(C6F5)(3)-Catalyzed Hydrodesulfurization Using Hydrosilanes - Metal-Free Reduction of Sulfides

Kodai Saito, Kazumi Kondo, Takahiko Akiyama

ORGANIC LETTERS, 17(13) 3366-3369, Jul, 2015
Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-quinolones by a Protecting-Group-Free Approach

Kodai Saito, Yuka Moriya, Takahiko Akiyama

ORGANIC LETTERS, 17(13) 3202-3205, Jul, 2015
Synthesis of 3-Aryl-1-trifluoromethyltetrahydroisoquinolines by Bronsted Acid-Catalyzed C(sp(3))-H Bond Functionalization

Keiji Mori, Nobuaki Umehara, Takahiko Akiyama

ADVANCED SYNTHESIS & CATALYSIS, 357(5) 901-906, Mar, 2015
Benzothiazoline: Versatile Hydrogen Donor for Organocatalytic Transfer Hydrogenation

Chen Zhu, Kodai Saito, Masahiro Yamanaka, Takahiko Akiyama

ACCOUNTS OF CHEMICAL RESEARCH, 48(2) 388-398, Feb, 2015
Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

Kodai Saito, Hiromitsu Miyashita, Takahiko Akiyama

CHEMICAL COMMUNICATIONS, 51(93) 16648-16651, 2015
Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking

Keiji Mori, Ayaka Miyake, Takahiko Akiyama

CHEMICAL COMMUNICATIONS, 51(89) 16107-16110, 2015
gamma-Silylboronates in the chiral Bronsted acid-catalysed allylboration of aldehydes

P. Barrio, E. Rodriguez, K. Saito, S. Fustero, T. Akiyama

CHEMICAL COMMUNICATIONS, 51(25) 5246-5249, 2015
Enantioselective Synthesis of Chiral Biaryl Chlorides/Iodides by a Chiral Phosphoric Acid Catalyzed Sequential Halogenation Strategy

Keiji Mori, Manato Kobayashi, Tsubasa Itakura, Takahiko Akiyama

ADVANCED SYNTHESIS & CATALYSIS, 357(1) 35-40, Jan, 2015
Asymmetric Transfer Hydrogenation of Ketimines by Indoline as Recyclable Hydrogen Donor

Kodai Saito, Hiromitsu Miyashita, Takahiko Akiyama

ORGANIC LETTERS, 16(20) 5312-5315, Oct, 2014
Chiral Bronsted Acid Catalysts

43(6) 7-13, Jun, 2014
Chiral Phosphoric-Acid-Catalyzed Transfer Hydrogenation of Ethyl Ketimine Derivatives by Using Benzothiazoline

Kodai Saito, Kosaku Horiguchi, Yukihiro Shibata, Masahiro Yamanaka, Takahiko Akiyama

CHEMISTRY-A EUROPEAN JOURNAL, 20(25) 7616-7620, Jun, 2014
Phosphoric Acid Bridged Cobalt Bis(dicarbollide) Ion as a Highly Efficient Catalyst for the Organocatalytic Hydrogenation of Ketimines

Takahiko Akiyama, Kodai Saito, Slawomir Janczak, Zbigniew J. Lesnikowski

SYNLETT, 25(6) 795-798, Apr, 2014
Double C(sp(3))-H Bond Functionalization Mediated by Sequential Hydride Shift/Cyclization Process: Diastereoselective Construction of Polyheterocycles

Keiji Mori, Kazuki Kurihara, Shinnosuke Yabe, Masahiro Yamanaka, Takahiko Akiyama

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 136(10) 3744-3747, Mar, 2014
The Bimolecular and Intramolecular Mannich and Related Reactions

T. Akiyama

Comprehensive Organic Synthesis: Second Edition, 2 629-681, Feb, 2014
Enantioselective Fluorination of beta-Ketoesters Catalyzed by Chiral Sodium Phosphate: Remarkable Enhancement of Reactivity by Simultaneous Utilization of Metal Enolate and Metal Phosphate

Keiji Mori, Ayaka Miyake, Takahiko Akiyama

CHEMISTRY LETTERS, 43(1) 137-139, Jan, 2014
Expeditious synthesis of 1-aminoindane derivatives achieved by [1,4]-hydride shift mediated C(sp(3))-H bond functionalization

Keiji Mori, Kazuki Kurihara, Takahiko Akiyama

CHEMICAL COMMUNICATIONS, 50(28) 3729-3731, 2014
Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel-Crafts reaction of indoles with beta,beta-disubstituted nitroalkenes

Keiji Mori, Manari Wakazawa, Takahiko Akiyama

CHEMICAL SCIENCE, 5(5) 1799-1803, 2014
Chiral Copper(II) Phosphate Catalyzed Enantioselective Synthesis of Isochromene Derivatives by Sequential Intramolecular Cyclization and Asymmetric Transfer Hydrogenation of o-Alkynylacetophenones

Kodai Saito, Yuki Kajiwara, Takahiko Akiyama

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 52(50) 13284-13288, Dec, 2013
Enantioselective Transfer Hydrogenation of Difluoromethyl Ketimines Using Benzothiazoline as a Hydrogen Donor in Combination with a Chiral Phosphoric Acid

Tsubasa Sakamoto, Kosaku Horiguchi, Kodai Saito, Keiji Mori, Takahiko Akiyama

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2(11) 943-946, Nov, 2013
Prediction of suitable catalyst by 1H NMR: Asymmetric synthesis of multisubstituted biaryls by chiral phosphoric acid catalyzed asymmetric bromination

Keiji Mori, Yuki Ichikawa, Manato Kobayashi, Yukihiro Shibata, Masahiro Yamanaka, Takahiko Akiyama

Chemical Science, 4(11) 4235-4239, Sep 30, 2013
Chiral Phosphoric Acid-Catalyzed Oxidative Kinetic Resolution of Indolines Based on Transfer Hydrogenation to Imines

Kodai Saito, Yukihiro Shibata, Masahiro Yamanaka, Takahiko Akiyama

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 135(32) 11740-11743, Aug, 2013
Molecular iodine catalyzed transfer hydrogenation: reduction of aldimines, ketimines, and alpha-imino esters

Prabhakar Bachu, Chen Zhu, Takahiko Akiyama

TETRAHEDRON LETTERS, 54(30) 3977-3981, Jul, 2013
Enantioselective Synthesis of Multisubstituted Biaryl Skeleton by Chiral Phosphoric Acid Catalyzed Desymmetrization/Kinetic Resolution Sequence

Keiji Mori, Yuki Ichikawa, Manato Kobayashi, Yukihiro Shibata, Masahiro Yamanaka, Takahiko Akiyama

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 135(10) 3964-3970, Mar, 2013
Asymmetric C-C Bond Formation Using Chiral Phosphoric Acid

Takahiko Akiyama

Asymmetric Synthesis II: More Methods and Applications, 261-266, Jan 14, 2013
Hydrodefluorinations of trifluorotoluenes by LiAlH4 and TiCl4

Takahiko Akiyama, Kohei Atobe, Michiko Shibata, Keiji Mori

Journal of Fluorine Chemistry, 152 81-83, 2013
Singapore visit report, observing trends and enhancing ties with Singapore in the field of organic synthesis

Takahiko Akiyama, Takeshi Yura

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 71(6) 639-641, 2013
6.3 C-C Bond Formation: Mannich Reaction

T. Akiyama

Comprehensive Chirality, 6 69-96, Sep, 2012
Kinetic Resolution in Chiral Phosphoric Acid Catalyzed Aldol Reactions: Enantioselective Robinson-Type Annulation Reactions

Masahiro Yamanaka, Masaya Hoshino, Takuya Katoh, Keiji Mori, Takahiko Akiyama

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (24) 4508-4514, Aug, 2012
Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Deuteration of Ketimines by Use of Benzothiazoline As a Deuterium Donor: Synthesis of Optically Active Deuterated Amines

Tsubasa Sakamoto, Keiji Mori, Takahiko Akiyama

ORGANIC LETTERS, 14(13) 3312-3315, Jul, 2012
Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp(3))-H Bond Functionalization and Its Application to Formal Synthesis of (+/-)-Tetrahydropalmatine

Keiji Mori, Taro Kawasaki, Takahiko Akiyama

ORGANIC LETTERS, 14(6) 1436-1439, Mar, 2012
Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor

Chen Zhu, Takahiko Akiyama

TETRAHEDRON LETTERS, 53(4) 416-418, Jan, 2012
Enantioselective organocatalytic reductive amination of aliphatic ketones by benzothiazoline as hydrogen donor

Kodai Saito, Takahiko Akiyama

CHEMICAL COMMUNICATIONS, 48(38) 4573-4575, 2012
Rapid Access to 3-Aryltetralin Skeleton via C(sp(3))-H Bond Functionalization: Investigation on the Substituent Effect of Aromatic Ring Adjacent to C-H Bond in Hydride Shift/Cyclization Sequence

Keiji Mori, Shosaku Sueoka, Takahiko Akiyama

CHEMISTRY LETTERS, 40(12) 1386-1388, Dec, 2011
Development of Chiral Bronsted Acid and its Application to Asymmetric Synthesis

Takahiko Akiyama

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 69(8) 913-925, Aug, 2011
Bronsted Acid Catalyzed Reductive Amination with Benzothiazoline as a Highly Efficient Hydrogen Donor

Chen Zhu, Takahiko Akiyama

SYNLETT, (9) 1251-1254, Jun, 2011
Bronsted Acid Catalyzed Reductive Amination with Benzothiazoline as a Highly Efficient Hydrogen Donor

Chen Zhu, Takahiko Akiyama

SYNLETT, (9) 1251-1254, Jun, 2011
Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of beta-Amino-alpha, alpha-difluoro Carbonyl Compounds

Wataru Kashikura, Keiji Mori, Takahiko Akiyama

ORGANIC LETTERS, 13(7) 1860-1863, Apr, 2011
Selective Activation of Enantiotopic C(sp(3))-Hydrogen by Means of Chiral Phosphoric Acid: Asymmetric Synthesis of Tetrahydroquinoline Derivatives

Keiji Mori, Kensuke Ehara, Kazuki Kurihara, Takahiko Akiyama

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 133(16) 6166-6169, Apr, 2011

Books and Other Publications

Germaniium in Organic Synthesis in "Main Group Metals in Organic Synthesis"

Wiley-VCH, 2004 (ISBN: 3527305084)

Professional Memberships

Research Projects

Development of novel catalytic reactions by combining chiral phosphoric acid and photochemistry

Grants-in-Aid for Scientific Research, Japan Society for the Promotion of Science, Apr, 2023 - Mar, 2026
New Development of Asymmetric Catalytic Reactions Using Chiral Phosphoric Acid

Grants-in-Aid for Scientific Research, Japan Society for the Promotion of Science, Apr, 2020 - Mar, 2023
On-demand asymmetric synthesis using the cooperative system of chiral phosphoric acid and photoredox catalyst

Grants-in-Aid for Scientific Research, Japan Society for the Promotion of Science, Apr, 2020 - Mar, 2022
軸性不斉を有するキラルビアリールの回転障壁を下げることは可能か？

科学研究費補助金挑戦的研究（萌芽）, 日本学術振興会, Apr, 2018 - Mar, 2020

秋山隆彦
キラルリン酸およびその誘導体を用いた不斉合成反応の新展開

科学研究費補助金基盤研究（B）, 日本学術振興会, Apr, 2017 - Mar, 2020

秋山隆彦

To the list screen