Organization
Institute of Transformative Bio-Molecules Designated Associate Professor
Graduate School
Graduate School of Engineering
Title
Designated Associate Professor
Contact information
External link
MUTO Kei
Degree 1
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Doctor of Science （ 2015.9 Nagoya University ）
Research Areas 2
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Nanotechnology/Materials / Synthetic organic chemistry
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Nanotechnology/Materials / Synthetic organic chemistry
Research History 5
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Nagoya University Institute of Transformative Bio-Molecules Designated Associate Professor
2024.6
Country：Japan
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Waseda University Institue for Advanced Study Associate Professor
2022.4 - 2024.5
Country：Japan
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Waseda University Waseda Institute for Advanced Study Lecturer
2020.4 - 2022.3
Country：Japan
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Waseda University Department of Applied Chemistry Lecturer
2018.4 - 2020.3
Country：Japan
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Waseda University Department of Applied Chemistry Assistant Professor
2016.4 - 2018.3
Country：Japan
Education 3
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Nagoya University Graduate School of Science Department of Chemistry
2013.4 - 2015.9
Country： Japan
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Nagoya University Graduate School of Science Department of Chemistry
2011.4 - 2013.3
Country： Japan
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Nagoya University School of Science Department of Chemistry
2007.4 - 2011.3
Country： Japan
Professional Memberships 6
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KINKA CHEMICAL SOCIETY
2017.9
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Chemistry Society of Japan
2011
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有機合成化学協会
2011
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The Society of Synthetic Organic Chemistry, Japan
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Chemical Society of Japan
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The Japanese Society for Process Chemistry
Papers 65
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Cross-Coupling of Aromatic Esters by Decarbonylation Reviewed
Muto K.; Yamaguchi J.
Amide Bond Activation: Concepts and Reactions page： 453 - 486 2022.10
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Synthesis and Properties of Pyridine-Fused Triazolylidene-Palladium: Catalyst for Cross-Coupling Using Chloroarenes and Nitroarenes Reviewed
Iizumi K.; Nakayama K.P.; Kato K.; Muto K.; Yamaguchi J.
Journal of Organic Chemistry Vol. 87 ( 17 ) page： 11909 - 11918 2022.8
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Identification of α-Synuclein Proaggregator: Rapid Synthesis and Streamlining RT-QuIC Assays in Parkinson's Disease Reviewed Open Access
Takada F.; Kasahara T.; Otake K.; Maru T.; Miwa M.; Muto K.; Sasaki M.; Hirozane Y.; Yoshikawa M.; Yamaguchi J.
ACS Medicinal Chemistry Letters Vol. 13 ( 9 ) page： 1421 - 1426 2022.8
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Pd-Catalyzed 1,4-Carboamination of Bicyclic Bromoarenes with Diazo Compounds and Amines Reviewed Open Access
Wu Q.; Muto K.; Yamaguchi J.
Organic Letters Vol. 24 ( 23 ) page： 4129 - 4134 2022.6
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Decarbonylative Reductive Coupling of Aromatic Esters by Nickel and Palladium Catalyst Reviewed Open Access
Peng Y.; Isshiki R.; Muto K.; Yamaguchi J.
Chemistry Letters Vol. 51 ( 7 ) page： 749 - 753 2022.5
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Convergent Azaspirocyclization of Bromoarenes with N-Tosylhydrazones by a Palladium Catalyst Reviewed Open Access
Yanagimoto A.; Uwabe Y.; Wu Q.; Muto K.; Yamaguchi J.
ACS Catalysis Vol. 11 page： 10429 - 10435 2021.8
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Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction Reviewed Open Access
Isshiki R.; Kurosawa M.B.; Muto K.; Yamaguchi J.
Journal of the American Chemical Society Vol. 143 ( 27 ) page： 10333 - 10340 2021.6
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Development of Pd-catalyzed denitrative couplings Reviewed
Asahara K.K.; Kashihara M.; Muto K.; Nakao Y.; Yamaguchi J.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry Vol. 79 ( 1 ) page： 11 - 21 2021.1
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Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst Invited Reviewed
Iizumi K.; Kurosawa M.B.; Isshiki R.; Muto K.; Yamaguchi J.
Synlett Vol. 32 ( 15 ) page： 1555 - 1559 2020.10
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Transition-Metal-Catalyzed Denitrative Coupling of Nitroarenes Reviewed Open Access
Muto K.; Okita T.; Yamaguchi J.
ACS Catalysis Vol. 10 ( 17 ) page： 9856 - 9871 2020.8
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Catalytic three-component C-C bond forming dearomatization of bromoarenes with malonates and diazo compounds Reviewed Open Access
Kato H.; Musha I.; Komatsuda M.; Muto K.; Yamaguchi J.
Chemical Science Vol. 11 ( 33 ) page： 8779 - 8784 2020.7
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Ester dance reaction on the aromatic ring Reviewed Open Access
Matsushita K.; Takise R.; Muto K.; Yamaguchi J.
Science Advances Vol. 6 ( 28 ) 2020.7
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Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds Reviewed Open Access
Kurosawa M.B.; Isshiki R.; Muto K.; Yamaguchi J.
Journal of the American Chemical Society Vol. 142 ( 16 ) page： 7386 - 7392 2020.4
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Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane Reviewed Open Access
Kayashima Y.; Komatsuda M.; Muto K.; Yamaguchi J.
Chemistry Letters Vol. 49 ( 7 ) page： 836 - 839 2020.4
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Dearomative Allylation of Naphthyl Cyanohydrins by Palladium Catalysis: Catalyst-Enhanced Site Selectivity Reviewed Open Access
Yanagimoto A.; Komatsuda M.; Muto K.; Yamaguchi J.
Organic Letters Vol. 22 ( 9 ) page： 3423 - 3427 2020.4
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Palladium-Catalyzed Mizoroki-Heck Reaction of Nitroarenes and Styrene Derivatives Reviewed Open Access
Okita T.; Asahara K.K.; Muto K.; Yamaguchi J.
Organic Letters Vol. 22 ( 8 ) page： 3205 - 3208 2020.4
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Ester Transfer Reaction of Aromatic Esters with Haloarenes and Arenols by a Nickel Catalyst Reviewed Open Access
Isshiki R.; Inayama N.; Muto K.; Yamaguchi J.
ACS Catalysis Vol. 10 ( 5 ) page： 3490 - 3494 2020.2
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Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones Reviewed
Ishitobi K.; Muto K.; Yamaguchi J.
ACS Catalysis Vol. 9 ( 12 ) page： 11685 - 11690 2019.11
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Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates Reviewed Open Access
Komatsuda M.; Kato H.; Muto K.; Yamaguchi J.
ACS Catalysis Vol. 9 ( 10 ) page： 8991 - 8995 2019.9
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Pd-Catalyzed Denitrative Intramolecular C-H Arylation Reviewed
Asahara K.K.; Okita T.; Saito A.N.; Muto K.; Nakao Y.; Yamaguchi J.
Organic Letters Vol. 21 ( 12 ) page： 4721 - 4724 2019.6
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Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates Reviewed
Komatsuda M.; Muto K.; Yamaguchi J.
Organic Letters Vol. 20 ( 14 ) page： 4354 - 4357 2018.7
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Synthesis of a heptaarylisoquinoline: Unusual disconnection for constructing isoquinoline frameworks Reviewed Open Access
Asako T.; Suzuki S.; Itami K.; Muto K.; Yamaguchi J.
Chemistry Letters Vol. 47 ( 8 ) page： 968 - 970 2018.6
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Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters Reviewed
Okita T.; Komatsuda M.; Saito A.N.; Hisada T.; Takahara T.T.; Nakayama K.P.; Isshiki R.; Takise R.; Muto K.; Yamaguchi J.
Asian Journal of Organic Chemistry Vol. 7 ( 7 ) page： 1358 - 1361 2018.5
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Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst Reviewed
Okita T.; Muto K.; Yamaguchi J.
Organic Letters Vol. 20 ( 10 ) page： 3132 - 3135 2018.5
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Pd-Catalyzed Decarbonylative C−H Coupling of Azoles and Aromatic Esters Reviewed
Matsushita K.; Takise R.; Hisada T.; Suzuki S.; Isshiki R.; Itami K.; Muto K.; Yamaguchi J.
Chemistry - An Asian Journal Vol. 13 ( 17 ) page： 2393 - 2396 2018.5
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Decarbonylative aryl thioether synthesis by Ni catalysis Reviewed
Ishitobi K.; Isshiki R.; Asahara K.K.; Lim C.; Muto K.; Yamaguchi J.
Chemistry Letters Vol. 47 ( 6 ) page： 756 - 759 2018.4
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Decarbonylative coupling reaction of aromatic esters Reviewed
Isshiki R.; Okita T.; Muto K.; Yamaguchi J.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry Vol. 76 ( 4 ) page： 300 - 314 2018.4
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Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds Reviewed
Isshiki R.; Muto K.; Yamaguchi J.
Organic Letters Vol. 20 ( 4 ) page： 1150 - 1153 2018.2
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Synthesis of fully arylated (hetero) arenes by coupling reaction Reviewed
Asako T.; Muto K.; Yamaguchi J.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry Vol. 76 ( 2 ) page： 98 - 110 2018.2
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Catalytic α-Arylation of Ketones with Heteroaromatic Esters Reviewed
Isshiki R.; Takise R.; Itami K.; Muto K.; Yamaguchi J.
Synlett Vol. 28 ( 19 ) page： 2599 - 2603 2017.10
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Cross-coupling of aromatic esters and amides Reviewed
Takise R.; Muto K.; Yamaguchi J.
Chemical Society Reviews Vol. 46 ( 19 ) page： 5864 - 5888 2017.7
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Synthesis of multiply arylated pyridines Invited Reviewed Open Access
Asako T.; Hayashi W.; Amaike K.; Suzuki S.; Itami K.; Muto K.; Yamaguchi J.
Tetrahedron Vol. 73 ( 26 ) page： 3669 - 3676 2017.4
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Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis Reviewed
Takise R.; Isshiki R.; Muto K.; Itami K.; Yamaguchi J.
Journal of the American Chemical Society Vol. 139 ( 9 ) page： 3340 - 3343 2017.2
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Palladium-catalyzed decarbonylative alkynylation of aromatic esters Reviewed
Okita T.; Kumazawa K.; Takise R.; Muto K.; Itami K.; Yamaguchi J.
Chemistry Letters Vol. 46 ( 2 ) page： 218 - 220 2016.11
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Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids Reviewed
Muto K.; Hatakeyama T.; Itami K.; Yamaguchi J.
Organic Letters Vol. 18 ( 19 ) page： 5106 - 5109 2016.9
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C-H arylation and alkenylation of imidazoles by nickel catalysis: Solvent-accelerated imidazole C-H activation Reviewed Open Access
Muto K.; Hatakeyama T.; Yamaguchi J.; Itami K.
Chemical Science Vol. 6 ( 12 ) page： 6792 - 6798 2015.9
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Decarbonylative organoboron cross-coupling of esters by nickel catalysis Reviewed International coauthorship Open Access
Muto K.; Yamaguchi J.; Musaev D.G.; Itami K.
Nature Communications Vol. 6 2015.6
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Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C-H/C-O biaryl coupling Reviewed International coauthorship
Muto K.; Yamaguchi J.; Lei A.; Itami K.
Journal of the American Chemical Society Vol. 135 ( 44 ) page： 16384 - 16387 2013.10
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Nickel-catalyzed C-H/C-O coupling of azoles with phenol derivatives Reviewed
Muto K.; Yamaguchi J.; Itami K.
Journal of the American Chemical Society Vol. 134 ( 1 ) page： 169 - 172 2011.12
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Nickel‐Catalyzed cine‐Substitution Toward Carbonyl Dance Open Access
Eito Moriya, Kei Muto, Junichiro Yamaguchi
Chemistry – An Asian Journal Vol. 21 ( 1 ) page： e00991 2026.1
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Facile generation of<i> ortho</i>-quinodimethanes toward polycyclic compounds Open Access
Inagaki, K; Onozawa, Y; Fukuhara, Y; Yokogawa, D; Muto, K; Yamaguchi, J
CHEM Vol. 11 ( 11 ) 2025.11
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Electrooxidative Ring-Opening Transformation of Polycyclic Aromatic Hydrocarbons
Ryosuke Sakamoto, Kei Muto, Junichiro Yamaguchi
Organic Letters Vol. 27 ( 43 ) page： 11974 - 11978 2025.10
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An Umpolung Approach for C2‐Selective C−H Amination of Azines by Palladium Catalysis Open Access
Qikun Wu, Kei Muto, Junichiro Yamaguchi
ChemistryEurope 2025.3
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6.1 Palladium-Catalyzed Dearomative Functionalization of Arenes
K. Muto, J. Yamaguchi
2025
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2H-Thiazolo[4,5-d][1,2,3]triazole: synthesis, functionalization, and application in scaffold-hopping Open Access
Ryuya Miyazaki, Fumito Takada, Takunari Kikuchi, Yuya Oguro, Makoto Kamata, Takafumi Yukawa, Kenta Kato, Kei Muto, Junichiro Yamaguchi
Chemical Science Vol. 15 ( 38 ) page： 15835 - 15840 2024.10
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Versatile deacylative cross-coupling of aromatic ketones Reviewed
Nakahara H.; Isshiki R.; Kubo M.; Iizumi K.; Muto K.; Yamaguchi J.
Chem Vol. 10 ( 9 ) page： 2916 - 2930 2024.9
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Cine-Substitution of Enolates: Enolate Dance/Coupling of Cycloalkenyl Pivalates by Nickel Catalysis
Eito Moriya, Kei Muto, Junichiro Yamaguchi
ACS Catalysis Vol. 14 ( 13 ) page： 10412 - 10417 2024.6
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Palladium-Catalyzed Denitrative Synthesis of Aryl Nitriles from Nitroarenes and Organocyanides Reviewed
Keiichiro Iizumi, Hiroki Tanaka, Kei Muto, Junichiro Yamaguchi
Organic Letters Vol. 26 ( 18 ) page： 3977 - 3981 2024.4
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Palladium-Catalyzed Synthesis of Bicyclic Derivatives from the Cyclization/1,4-Difunctionalization of Bromoarenes with Diazo Compounds Invited Reviewed
Hiroki Kato, Yuki Fukuhara, Ryuya Miyazaki, Kei Muto, Junichiro Yamaguchi
Asian Journal of Organic Chemistry Vol. 13 ( 2 ) page： e202300548 2024.2
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Pd- Catalyzed Dearomative Functionalizations of Benzyl and Aryl ElectroPhiles
Kato, H; Muto, K; Yamaguchi, J
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN Vol. 82 ( 10 ) page： 965 - 978 2024
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Concise Synthesis of (±)-Fortuneicyclidins and (±)-Cephalotine B Enabled by Pd-Catalyzed Dearomative Spirocyclization Invited Reviewed Open Access
Yota Uwabe, Kei Muto, . Junichiro Yamaguchi
Chemistry-A European Journal Vol. 29 ( 68 ) page： e202302769 2023.9
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Chloroacetyl Boronate N-Tosylhydrazone as a Versatile Synthetic Building Block Invited Reviewed Open Access
Chemical Communications Vol. 59 ( 48 ) page： 7419 - 7422 2023.5
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Pd-Catalyzed Denitriative Intramolecular Mizoroki–Heck Reaction Reviewed
Kitty K Asahara, Kei Muto, Junichiro Yamaguchi
Chemistry Letters Vol. 52 ( 4 ) page： 299 - 302 2023.3
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Aryl sulfide synthesis via aryl exchange reaction Invited Reviewed Open Access
Trends in Chemistry Vol. 5 ( 1 ) page： 102 - 103 2022.10
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Unified Synthesis of Multiply Arylated Alkanes by Catalytic Deoxygenative Transformation of Diarylketones Reviewed Open Access
Kurosawa, M. B.; Kato, K.; Muto, K.; Yamaguchi, J.
Chemical Science Vol. 13 ( 36 ) page： 10743 - 10751 2022.8
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Catalytic enantioselective dihalogenation reaction of alkene Reviewed Open Access
Muto K.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry Vol. 74 ( 12 ) page： 1225 - 1226 2016.12
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Nickel-Catalyzed Aromatic C–H Functionalization Reviewed
Yamaguchi J.; Muto K.; Itami K.
Topics in Current Chemistry Vol. 374 ( 4 ) 2016.8
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C-H activation generates period-shortening molecules that target cryptochrome in the mammalian circadian clock Reviewed International coauthorship
Oshima T.; Yamanaka I.; Kumar A.; Yamaguchi J.; Nishiwaki-Ohkawa T.; Muto K.; Kawamura R.; Hirota T.; Yagita K.; Irle S.; Kay S.A.; Yoshimura T.; Itami K.
Angewandte Chemie - International Edition Vol. 54 ( 24 ) page： 7193 - 7197 2015.5
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Key mechanistic features of Ni-catalyzed C-H/C-O biaryl coupling of azoles and naphthalen-2-yl pivalates Reviewed International coauthorship
Xu H.; Muto K.; Yamaguchi J.; Zhao C.; Itami K.; Musaev D.G.
Journal of the American Chemical Society Vol. 136 ( 42 ) page： 14834 - 14844 2014.9
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Nickel-catalyzed α-arylation of ketones with phenol derivatives Reviewed
Takise R.; Muto K.; Yamaguchi J.; Itami K.
Angewandte Chemie - International Edition Vol. 53 ( 26 ) page： 6791 - 6794 2014.5
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C-H alkenylation of azoles with enols and esters by nickel catalysis Reviewed
Meng L.; Kamada Y.; Muto K.; Yamaguchi J.; Itami K.
Angewandte Chemie - International Edition Vol. 52 ( 38 ) page： 10048 - 10051 2013.7
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Nickel-catalyzed direct coupling of heteroarenes Reviewed
Yamaguchi J.; Muto K.; Amaike K.; Yamamoto T.; Itami K.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry Vol. 71 ( 6 ) page： 576 - 587 2013.6
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Recent progress in nickel-catalyzed biaryl coupling Reviewed
Yamaguchi J.; Muto K.; Itami K.
European Journal of Organic Chemistry ( 1 ) page： 19 - 30 2012.9
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Decarbonylative C-H coupling of azoles and aryl esters: Unprecedented nickel catalysis and application to the synthesis of muscoride A Reviewed
Amaike K.; Muto K.; Yamaguchi J.; Itami K.
Journal of the American Chemical Society Vol. 134 ( 33 ) page： 13573 - 13576 2012.8
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Nickel-catalyzed C-H arylation of azoles with haloarenes: Scope, mechanism, and applications to the synthesis of bioactive molecules Reviewed
Yamamoto T.; Muto K.; Komiyama M.; Canivet J.; Yamaguchi J.; Itami K.
Chemistry - A European Journal Vol. 17 ( 36 ) page： 10113 - 10122 2011.7
Books 1
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New Cross-coupling Reactions through Nickel Catalysis
Junichiro Yamaguchi, Kazuma Amaike, Kei Muto, Kenichiro Itami
Presentations 3
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Organic Synthesis Playing with The Unique Reactivity of Benzyl–Palladium Invited
Kei Muto
Osaka Unviersity 2024.5.18
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Organic Synthesis Playing with The Unique Reactivity of Benzyl–Palladium Invited
Kei Muto
2024.5.11
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Multi-Dimensional Transformation of Aromatic Compounds through Benzyl–Palladium Invited
Kei Muto
Nagoya University 2024.4.15
KAKENHI (Grants-in-Aid for Scientific Research) 2
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触媒的かつ収束的なオルトキノジメタンの発生法と迅速多環式骨格構築
Grant number：24K01491 2024.4 - 2028.3
日本学術振興会 科学研究費助成事業 基盤研究(B)
武藤 慶
Authorship：Principal investigator
Grant amount：\18590000 （ Direct Cost: \14300000 、 Indirect Cost：\4290000 ）
本研究では有用な短寿命高活性種であるオルトキノジメタン(oQDM)を触媒的かつ収束的に発生させる新規手法の確立を目的とする。生成したoQDMを系中にジエノフィルを共存させることでDiels-Alder反応させ多様な多環式分子合成へ展開する。本研究では、ベンジルパラジウム触媒中間体の特異な遠隔位での結合形成/切断反応の誘起と制御を鍵とし、普遍的な化学原料の多成分連結でoQDMを発生させる、新規手法を確立する。特殊な前駆体の調製を要した従来のoQDM化学を一変しうる革新的手法であり、複雑な多環式骨格を一挙に形成できる驚き反応を提供する。
有機合成化学的に有用な反応中間体であるオルトキノジメタン種を、入手容易性の高い化学原料の触媒的な多成分連結で発生させる新規手法を開発し、それを用いた多環式化合物の迅速かつ多様性合成法の開発を目的に研究した。オルトキノジメタンがCavaらに発見されてから約70年間、この化学種の反応性を用いた有機合成は大きな進展を遂げ、この化学種を活用した複雑な構造の天然物合成がいくつも報告されてきた。しかし、オルトキノジメタンの発生方法に関しては、煩雑かつ多工程を要する前駆体調製を必要する点、さらに、その前駆体から過酷な反応条件下でオルトキノジメタンを発生させる必要があるといった課題があった。この課題は、目的化合物の合成を全体的に多工程化させてしまい、真に効率的な合成経路の立案に際して障害となっていた。この課題の解決には、従来法とは一線を画す、新規基本的方法論の提示が重要となる。
当該年度では、申請当初に見いだしていた初期検討結果を大きく進展させた。具体的には、2-ブロモスチレン、ジアゾ化合物、ジエステル求核剤をパラジウム触媒を用いて多成分連結することでオルトキノジメタンを高収率で生成させ、その後分子内Diels-Alder反応を進行させることで良好な収率とジアステレオ選択性で目的の多環式化合物を得られることができた。この３つの化学種の連結に加え、4つの化学種を連結させる、より多様性創出に富んだ合成法も見出した。実際に、ステロイド天然物の迅速合成にも本手法が有効であることを実証し、合成的価値を十分に示すこともできている。また、本多成分連結反応が如何にして進行するかを計算化学と実験化学の両面から探究し、ベンジルパラジウム触媒中間体の前例のないπ-アリルパラジウムへの異性化機構を伴って進行していることも突き止めた。
2024年度に、上述の三成分連結反応の開発と実践的合成への応用を達成できた。それに加え、次年度に実施する予定だった本反応の反応機構解明研究を実施でき、重要な知見を得ることもできた。これらの成果をまとめ、すでに論文投稿もできている。本報告を記入時点で、論文訂正中の状態であり、受理間近である。本論文の内容以外にも、本成果を基に検討した結果、次の成果につながる研究の芽を数例見出すことができている。以上の理由から、「当初の計画以上に進展している」とした。
本方法論の不斉化は、見出した反応の真価、得られる生成物の価値を高めるために重要な課題となる。不斉化の検討を進める予定である。不斉反応を実現するに際し、キラルパラジウム触媒を開発すること、またはキラルなルイス酸を協働させ、不斉Diels-Alder反応を進行させる２つの戦略を計画している。また、2-ブロモスチレン以外の化合物を出発原料に用いる新手法の開発への展開も可能と考えており、2025年度に実施することを考えている。 -
Catalytic arene difunctionalizations through benzyl-Pd chemistry
Grant number：21K05079 2021.4 - 2024.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)