Eiji Yamaguchi

講師 山口 英士

Associated Professor Eiji Yamaguchi

E-mail yamaguchi[at]gifu-pu.ac.jp

【経歴】

2006年 3月 岐阜大学 工学部応用化学科 卒業 (村井利昭教授、芝原  文利 准教)

2008年 3月 岐阜大学 工学研究科 応用化学専攻 修士課程修了 (村井利昭教授、芝原  文利 准教)

2008年6月~2008年10月 The University of Texas at Austin, Department of Chemistry and Biochemistry  留学 (Prof. Michael J. Krische)

2008年 11月~2008年 12月 大阪大学 工学研究科 応用化学専攻  国内留学 (茶谷 直人 教授)

2011年 3月 岐阜大学 工学研究科 物質工学専攻 博士後期課程 修了 (村井利昭教授、芝原  文利 准教)

2011年 4月~2011年 10月 岐阜大学 特別研究補佐員 (村井利昭教授、芝原  文利 准教)

2011年6月~2013年 4月 The University of Texas at Austin, Department of Chemistry and Biochemistry 博士研究員 (Prof. Michael J. Krische)

2013年 5月~2014年 3月名古屋大学 大学院 理学研究科 物質理学専攻 博士研究員 (伊丹 健一郎 教授)

2014年 4月 岐阜薬科大学 創薬科学大講座 合成薬品製造学 研究室 助教

2018年 12月 岐阜薬科大学 創薬科学大講座 合成薬品製造学 研究室 講師

【受賞歴】
2007年 5月 The 4th International Symposium on Integrated Synthesis (ISIS-4) ポスター賞 2011年3月
平成22年度岐阜大学学長表彰
平成29年度有機合成化学協会東海支部奨励賞

【専門分野】
有機合成化学、有機金属化学

【comment】
犬、草、壁、雪が好きです。

【発表論文】

[61]

[60]

[59] Discovery and SAR of Natural-Product-Inspired RXR Agonists with Heterodimer Selectivity to PPARδ-RXR
K. Nakashima, E. Yamaguchi, C. Noritake, Y. Mitsugi, M. Goto, T. Hirai, N. Abe, E. Sakai, M. Oyama, A. Itoh, M. Inoue
ACS Chem. Biol. 202015, 1526-1534.
DOI: 10.1021/acschembio.0c00146

[58] The Novel gem-Dihydroperoxide 12AC3O Suppresses High Phosphate-Induced Calcification via Antioxidant Effects in p53LMAco1 Smooth Muscle Cells
K. Takase, M. Inden, S. Hirai, Y. Yamada, H. Kurita, M. Takeda, E. Yamaguchi, A. Itoh, I. Hozumi
Int. J. Mol. Sci. 202021, 4628-4643.
DOI: 10.3390/ijms21134628

[57] Transition‐Metal‐Free Synthesis of Phenanthridinones through Visible‐Light‐Driven Oxidative C–H Amidation
K. Usami, E. Yamaguchi, N. Tada, A. Itoh
Eur. J. Org. Chem. 2020, 1496-1504.
DOI: 10.1002/ejoc.201900536

[56] Visible light/molecular iodine-mediated diastereoselective intermolecular lactonization of styrenes with carbonyls
K. Oe, M. Goto, S. Maejima. E. Yamaguchi, A. Itoh
Asian J. Org. Chem. 2020, 571-574.
DOI: 10.1002/ajoc.202000041

[55] Regioselective carboiodination of styrenes: N-iodosuccinimide affords complete reaction regioselectivity
M. Goto, S. Maejima. E. Yamaguchi, A. Itoh
Asian J. Org. Chem. 20209, 210-213.
DOI: 10.1002/ajoc.202000022

[54] Synthesis of Indolines via a Photocatalytic Intramolecular Reductive Cyclization Reaction
E. Yamaguchi, Y. Goto, A. Itoh
Heterocycles 2020101, 177-185.
DOI: 10.3987/COM-19-S(F)8

[53] Nickel catalyzed intermolecular carbonyl addition of aryl halide
S. Ishida, H. Suzuki, S. Uchida, E. Yamaguchi, A. Itoh
Eur. J. Org. Chem. 2019, 2019, 7483-7487.
DOI:10.1002/ejoc.201901367

[52] Direct lactonization from 1,3-dienes and malonate esters mediated by a combination of iodine and visible light
M. Takeda, S. Maejima, E. Yamaguchi, A. Itoh
Tetrahedron Lett. 2019, 60, 151284.
DOI:10.1016/j.tetlet.2019.151284

[51] Inhibitory effects of 4-hydroperoxy-2-decenoic acid ethyl ester on phorbol ester- and TGF-β1-induced MMPs expression
T. Kamiya, M. Tanaka, H. Hara, E. Yamaguchi, A. Itoh, T. Adachi
Free radical Res. 2019, 53, 1051-1059.
DOI:10.1080/10715762.2019.1675874

[50] Visible light/Molecular iodine mediated intermolecular spirolactonization reaction of olefins with cyclic ketones
S. Maejima, E. Yamaguchi, A. Itoh
J. Org. Chem. 201984, 9519-9531.
DOI: 10.1021/acs.joc.9b01081

[49] Metal‐Free Oxidative Amidation of Aromatic Aldehydes using an Anthraquinone‐based Organophotocatalyst
H. Inagawa, S. Uchida, E. Yamaguchi, A. Itoh
Asian J. Org. Chem. 2019, 8, 1411-1414.
DOI: 10.1002/ajoc.201900256

[48]  Ruthenium polypyridyl complex-catalysed aryl alkoxylation of styrenes: Improving reactivity using a continuous flow photomicroreactor
E. Yamaguchi, N. Taguchi, A. Itoh
React. Chem. Eng. 20194, 995-999.
DOI: 10.1039/C9RE00061E

[47] Trans-diastereoselective syntheses of γ-lactones by visible light-iodine mediated carboesterification of alkenes
S. Maejima, E. Yamaguchi, A. Itoh
ACS Omega 20194, 4856-4870.
DOI: 10.1021/acsomega.9b00333

[46] Single-electron-transfer-initiated sequential direct arylation reaction of pyrrole with aryl diazonium salts
E. Yamaguchi, Y. Kashima, A. Itoh
Asian. J. Org. Chem. 20198, 324-327.

[45] Olefin bifunctionalization: A visible‐light‐photoredox‐catalyzed aryl alkoxylation of olefins
E. Yamaguchi, W. Tanaka, A. Itoh
Chem. Asian. J. 2019, 14, 121-124.

[44] Atom-transfer radical addition photocatalysis using a heteroleptic copper complex
K. Matsuo, E. Yamaguchi, A. Itoh
Asian J. Org. Chem. 2018, 7, 2435-2438.

[43] Induction of Human-Lung-Cancer-A549-Cell Apoptosis by 4-Hydroperoxy-2-decenoic Acid Ethyl Ester through Intracellular ROS Accumulation and the Induction of Proapoptotic CHOP Expression
T. Kamiya, M. Watanabe, H. Hara, Y. Mitsugi, E. Yamaguchi, A. Itoh, T. Adachi
J. Agric. Food Chem. 2018, 66, 10741-10747.

[42] Effects of gem-dihydroperoxides against mutant copper‑zinc superoxide dismutase-mediated neurotoxicity
T. Ueda, M. Inden, Y. Asaka, Y. Masaki, H. Kurita, W. Tanaka, E. Yamaguchi, A. Itoh, I. Hozumi
Mol. Cell. Neurosci. 2018, 82, 177-184.

[41] Visible-Light-Mediated Iminyl Radical Generation from Benzyl Oxime Ether: Synthesis of Pyrroline via Hydroimination Cyclization
K. Usami, E. Yamaguchi, N. Tada, A. Itoh
Org. Lett. 2018, 20, 5714–5717.

[40] Synthesis of Bicyclic Lactones via I2-Mediated Intramolecular tandem C–C/C–O Bond Formation
S. Maejima, M. Osuka, E. Yamaguchi, A. Itoh
Tetrahedron 201874, 2985-2990.

[39] A Radical Reaction for the Synthesis of 3‐Substituted Dihydrothiopyrans under Photosensitized Conditions
A. Fujiya, E. Yamaguchi, N. Tada, A. Itoh
Asian J. Org. Chem. 2018 6, 1061-1065.

[38] Photooxidative Keto-Trifluoromethylation of Styrenes by Means of an Anthraquinone-Based Organocatalyst
E. Yamaguchi, Y. Kamito, K. Matsuo, J. Ishihara, A. Itoh
Synthesis 201850, 3161-3168.

[37] Organic dye-catalyzed radical ring expansion reaction
M. Deguchi, A. Fujiya, E. Yamaguchi, N. Tada, A. Itoh
RSC Advances 2018, 8, 15825-15830.

[36] Aerobic Photooxidative Synthesis of β‐Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base
Y. Asano, Y. Nagasawa, E. Yamaguchi, A. Itoh
Chem.  Asian J. 201813, 409-412.

[35] Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities
K. Kawaai, T. Yamaguchi, E. Yamaguchi, S. Endo, N. Tada, A. Ikari, A. Itoh
J. Org. Chem. 2018, 83, 1988-1996.

[34] Synthesis, Characterization, and Reaction of a Both Inter- and Intramolecularly Coordinated Pseudocyclic Iodosylbenzene Trifluoroacetic Acid Complexes
M. Yudasaka, T. Maruyama, E. Yamaguchi, N, Tada, A. Itoh
Eur. J. Org. Chem. 20184, 550-556.

[33] Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ-Lactones Mediated by Molecular Iodine under Visible Light Irradiation
S. Maejima, E. Yamaguchi, A. Itoh
Adv. Synth. Catal. 2017, 359, 3883-3887.

[32] 4-Hydroperoxy-2-decenoic acid Ethyl Ester Protects Against 6-Hydroxydopamine-Induced Cell Death via Activation of Nrf2-ARE and eIF2α-ATF4 Pathways
Y. Inoue, H. Hara, Y. Mitsugi, E. Yamaguchi, T. Kamiya, A. Itoh, Tetsuo Adachi
Neurochemistry International 2018112, 288-296.

[31] Photo-oxidative Cross-Dehydrogenative Coupling-Type Reaction of Thiophenes with α-Position of Carbonyls Using a Catalytic Amount of Molecular Iodine
Y. Sudo, E. Yamaguchi, A. Itoh Akichika, Org. Lett. 201719, 1610-1613.

[30] Cross-Dehydrogenative C–H Amination of Indoles under Aerobic Photo-oxidative Conditions
T. Yamaguchi, E. Yamaguchi, A. Itoh
Org. Lett. 201719, 1282-1285.

[29] Synthetic  Method for the Preparation of Quinazolines by the Oxidation of Amines Using Singlet Oxygen
T. Yamaguchi, Y. Sugiura, E. Yamaguchi, N. Tada, A. Itoh
Asian J. Org. Chem. 20176, 432-435

[28]Rare Metal-Free Photo-Aerobic Intramolecular Dehydrogenative Cyclization Reaction towards Polycyclic Heteroarenes
E. Yamaguchi, Y. Sudo, N. Tada, A. Itoh
Adv. Synth. Catal. 2016358, 3191-3195.

[27]One-Pot Aerobic Photooxidative Darzens Reaction from Styrene and Benzyl Alcohol via Phenacyl Iodide and Benzaldehyde by Using­ Iodine
R. Omura, A. Fujiya, E. Yamaguchi, N. Tada, T. Miura, A. Itoh
Synthesis. 201648, 3971-3975.

[26]An Efficient Aziridination of Styrenes Promoted by Visible Light
K. Matsuzawa, Y. Nagasawa, E. Yamaguchi, N. Tada, A. Itoh
Synthesis 201648, 2845-2850.

[25]Sequential Photo-oxidative [3+2] Cycloaddition/Oxidative Aromatization Reactions for the Synthesis of Pyrrolo[2,1-a]isoquinolines Using Molecular Oxygen as the Terminal Oxidant
A. Fujiya, M. Tanaka, E. Yamaguchi, N. Tada, A. Itoh
J. Org. Chem. 201681, 7262-7270.

[24]One-pot epoxidation of alkenes using aerobic photoperoxidation of toluenes
M. Taguchi, Y. Nagasawa, E. Yamaguchi, N. Tada, A. Itoh
Tetrahedron Lett. 201657, 230-232.

[23]Magnesium iodide-catalyzed synthesis of 2-substituted quinazolines using molecular oxygen and visible light
T. Yamaguchi, K. Sakairi, E. Yamaguchi, N. Tada, A. Itoh
RSC Adv. 20166, 56892-56895.

[22]Synthesis of 2-hydroxymalonic acid derivatives via tandem oxidation and rearrangement by photo organic catalysis
A. Okada, Y. Nagasawa, T. Yamaguchi, E. Yamaguchi, N. Tada, A. Itoh
RSC Adv. 20166, 42596-42599.

[21]Royal Jelly Constituents Increase the Expression of Extracellular Superoxide Dismutase through Histone Acetylation in Monocytic THP-1 Cells
J. Makino, R. Ogasawara, T. Kamiya, H. Hara, Y. Mitsugi, E. Yamaguchi, A. Itoh, T. Adachi
J. Nat. Pro. 201679, 1137-1143.

[20]Intermolecular Cyclopropanation of Styrenes Using Iodine and Visible Light via Carbon–Iodine Bond Cleavage
K. Usami, Y. Nagasawa, E. Yamaguchi, N. Tada, A. Itoh
Org. Lett. 201618, 8-11.

[19]Direct ortho-Hydroxylation of 2-Phenylpyridines using Palladium(II) Chloride and Hydrogen Peroxide
T. Yamaguchi, E. Yamaguchi, N. Tada, A. Itoh
Adv. Synthcatal.2015, 3572017-2021.

[18]Aerobic photooxidative direct asymmetric aldol reactions of benzyl alcohols using water as the solvent
A. Fujiya, T. Nobuta, E. Yamaguchi, N. Tada, T. Miura, A. Itoh
RSC Adv., 20155, 39539-39543.

[17]Facile and efficient synthesis of hydroxyalkyl esters from cyclic acetals through aerobic photo-oxidation using anthraquinone-2-carboxylic acid
T. Yamaguchi, Y. Kudo, S. Hirashima, E. Yamaguchi, N. Tada, T. Miura, A. Itoh
Tetrahedron Letters, 201556, 1973-1975.

[16]Metal-free synthesis of imidazopyridine from nitroalkene and 2-aminopyridine in the presence of a catalytic amount of iodine and aqueous hydrogen peroxide
Y. Tachikawa, Y. Nagasawa, S. Furuhashi, L. Cui, E. Yamaguchi, N. Tada, T. Miura, A. Itoh
RSC Adv., 20155, 9591-9593.

[15]A Study of Aerobic Photooxidation with a Continuous-Flow Microreactor
N. Yoshitomo, T. Katsuya, T. Norihiro, E. Yamaguchi, A. Itoh
Synlett 201526, 412-415.

[14]Aerobic Photooxidative Synthesis of Phenols from Arylboronic Acids Using 2-Propanol as Solvent
K. Matsui, T. Ishigami, T. Yamaguchi, E. Yamaguchi. N. Tada, T. Miura, A. Itoh
Synlett 201425, 2613-2616.

[13]Copper-Catalyzed C-H Bond Direct Chalcogenations of Aromatic Compounds Leading to Diaryl sulfides, Selenides and Diselenides by Using Elemental Sulfur and Selenium as Chalcogen Sources under Oxidative Conditions
Fumitoshi Shibahara, Takafumi Kanai, Takafumi, Eiji Yamaguchi, Akika Kamei and Toshiaki Murai
Chem. Asian. J. 2014, 9(1), 237.
doi: 10.1002/asia.201300882

[12]  Direct C-C Coupling of α-Olefins and Styrenes to 3-Hydroxy-2-oxindoles via Ruthenium Catalyzed Hydrohydroxyalkylation: Byproduct-Free Conversion of Secondary to Tertiary Alcohols
Eiji Yamaguchi, Jeffrey Mowat, Tom Luong and Michael J. Krische
Angew. Chem. Int. Ed. 2013, 52(32), 8428-8431.
doi: 10.1002/anie.201303552

[11]  Ruthenium Catalyzed Hydroaminoalkylation of Isoprene via Transfer Hydrogenation: Byproduct-free Prenylation of Hydantoins
Daniel C. Schmitt, Jungyong Lee, Anne-Marie R. Dechert-Schmitt, Eiji Yamaguchi and Michael J. Krische
Chem. Commun. 2013, 49(54), 6096-6098.
doi: 10.1039/C3CC43463J

[10] Chiral Anion Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium Catalyzed Butadiene Hydrohydroxyalkylation
Emma L. McInturff, Eiji Yamaguchi and Michael J. Krische
J. Am. Chem. Soc. 2012, 134(51), 20628.
doi: 10.1021/ja311208a

[9] Enantioselective C-H Crotylation of Primary Alcohols via Hydrohydroxyalkylation of Butadiene Jason R. Zbieg, Eiji Yamaguchi, Emma L. McInturff and Michael J. Krische
Science, 2012,336(6079), 324-327.
doi: 10.1126/science.1219274
Highlighted in SYNFACTS
Highlighted in C&E NEWS (2012, March, 26, p. 46)

Highlighted in Japanese Scientist in Science 2012

[8]  One-pot Sequential Direct C-H Bond Arylation of Azoles Catalyzed by [Pd(phen)2](PF6)2
Funitoshi Shibahara, Takayuki Yamauchi, Eiji Yamaguchi and Toshiaki Murai
J. Org. Chem. 2012, 77(19), 8815-8820.
doi: 10.1021/jo301621t

[7]1-Alkynyl- and 1-Alkenyl-3-arylimidazo[1,5-a]pyridines: Synthesis, Photophysical Properties, and Observation of a Linear Correlation Between the Fluorescent Wavelength and Hammett Substituent Constants
Eiji Yamaguchi、Funitoshi Shibahara and Toshiaki Murai
J. Org. Chem. 2011,76(15), 6146-6158.
doi: 10.1021/jo200864x
Highlighted in ChemInform

[6] Direct Sequential C3 and C1 Arylation Reaction of Imidazo[1,5-a]pyridine Catalyzed by a 1,10-Phenanthroline Palladium Complex
Eiji Yamaguchi、Funitoshi Shibahara and Toshiaki Murai
Chem. Lett. 2011, 40(9), 939-940.
doi: 10.1021/jo200067y

[5] Direct Arylation of Simple Azoles Catalyzed by 1,10-Phenanthroline Containing Palladium Complexes: An Investigation of C4 Arylation of Azoles and the Synthesis of Triarylated Azoles by Sequential Arylation
Funitoshi Shibahara、Eiji Yamaguchi and Toshiaki Murai
 J. Org. Chem. 2011,76(8), 2680-2693.
doi: 10.1021/jo200067y

[4] Direct Multiple C-H Bond Arylation Reaction of Heteroarenes Catalyzed by Cationic Palladium Complex Bearing 1,10-Phenanthroline
Funitoshi Shibahara、Eiji Yamaguchi and Toshiaki Murai
Chem. Commun. 2010,46(14), 2471-2473.
doi: 10.1039/b920794e

[3]  Synthesis of 1,3-Diarylated Imidazo[1,5-a]pyridines with a Combinatorial Approach: Metal-Catalyzed Cross-Coupling Reactions of 1-Halo-3-Arylimidazo- [1,5-a]pyridines with Aryl metal Reagents
Funitoshi Shibahara, Eiji Yamaguchi, Asumi Kitagawa, Akio Imai and Toshiaki Murai
Tetrahedron 2009,65(26), 5062-5073.
doi: 10.1016/j.tet.2009.02.062

[2] Synthesis of Fluorescent 1,3-Diarylated Imidazo[1,5-a]pyridines: Oxidative Condensation- Cyclization of Aryl-2-Pyridylmethylamines and Aldehydes with Elemental Sulfur as an Oxidant”
Funitoshi Shibahara, Rie Sugiura, Eiji Yamaguchi, Asumi Kitagawa and Toshiaki Murai
J. Org. Chem. 2009,74(9), 3566-3568.
doi: 10.1021/jo900415y

[1] Synthesis of 2-Azaindolizines by Using an Iodine-Mediated Oxidative Desulfurization Promoted Cyclization of N-2-Pyridylmethyl Thioamides and an Investigation of Their Photophysical Properties
Funitoshi Shibahara, Asumi Kitagawa, Eiji Yamaguchi and Toshiaki Murai
Org. Lett. 2006, 8(24), 5621-5624.
doi: 10.1021/ol0623623

【講演歴】

[1] 若手研究者のためのセミナー 信州大学

【外部資金】

H26-H27年度 科学研究費 研究活動スタート支援 「可視光増感性触媒を利用する分子変換反応の開発:課題番号26893221」:代表 (2,730 千円)

H27-H28年度 公益財団法人旭硝子財団研究助成 「ヨウ素触媒を利用した炭素-炭素結合形成反応」:代表 (2,000 千円)

H27-H28年度 公益財団法人武田科学振興財団研究助成 「新奇ラジカル種の発生方法を鍵とした複雑分子の迅速合成法の開発」:代表 (2,000 千円)

H28年度 小川科学技術財団研究助成 「遷移金属触媒を利用する炭素‐水素結合の直接不斉酸化反応の開発」:代表 (500 千円)

H29年度 小川科学技術財団研究助成 「新規Ni錯体による触媒的Grignard反応:有機化学の新たなマイルストーン」:代表 (1,000 千円)

H30-R1年度 科学研究費若手研究「新奇求核性炭素原子を有するニッケル錯体の創成と触媒反応への応用:課題番号18K14871」:代表 (4,160 千円)

H30-R1年度 加藤記念バイオサイエンス振興財団 研究助成 「ヨウ素触媒による分子間 C–C 結合形成反応を鍵とする三次元複雑骨格の迅速 合成法の開発」:代表 (2,000 千円)

  R1 -R2年度 越山科学技術振興財団研究助成「有機光触媒による多電子酸化を経る多環芳香族炭化水素類の直裁合成法の開発」:代表 (2,000 千円)

R1-R2年度 公益財団法人住友財団基礎科学研究助成 「ハロゲン結合を鍵とした新規有機光触媒の新展開」:代表 (1,500 千円)

R2-R4年度 科学研究費基盤研究(C)「新規量子ドット光触媒の利用と創薬有機化学の新展開研究課題:課題番号20K06968」:代表 (4,420 千円)

R2-R4年度 公益財団法人武田科学振興財団研究助成 「ハロゲン結合を鍵とした光触媒のリデザイン:直接活性化経路による超効率分子変換法への応用」:代表 (2,000 千円)