Grant-in-Aid for Scientific Research on Innovative AreasPrecise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions

Junichiro Yamaguchi » Japanese

Affiliation Waseda University
Position Professor
Contact Email
HP http://www.jyamaguchi-lab.com/en/
Speciality Organic Chemistry, Organic Synthesis
Keyword Cross-Coupling Reaction, Transition-metal catalyst, Aromatic carboxylic acid
Institute The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan, The Kinki Chemical Society, Japan, American Chemical Society, Japanese society for chemical biology

Abstract

Development of Decarbonylative cross-coupling reaction of esters

Achievement

Printer friendly view

Original papers

  • "Ester Transfer Reaction of Aromatic Esters with Haloarenes and Arenols by a Nickel Catalyst"
    Isshiki, R.; Inayama, N.; Muto, K.; Yamaguchi, J.*
    ACS Catal., 2020, 10, 3490-3494
  • "Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst"
    Hoshi, T.; Ota, E.; Inokuma, Y.; Yamaguchi, J.*
    Org. Lett. , 2019, 21, 10081–10084
  • "Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones"
    Ishitobi, K.; Muto, K.; Yamaguchi, J.*
    ACS Catal., 2019, 9, 11685-11690
  • "Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates"
    Komatsuda, M.; Kato, H.; Muto, K.; Yamaguchi, J.*
    ACS Catal., 2019, 9, 8991–8995
  • "Pd-Catalyzed Denitrative Intramolecular C–H Arylation"
    Asahara, K. K.; Okita, T.; Saito, A. N. Muto, K.; Nakao, Y.; Yamaguchi, J.*
    Org. Lett. , 2019, 21, 4721-4724
  • "Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates"
    Komatsuda, M.; Muto, K.*; Yamaguchi, J.*
    Org. Lett. , 2018, 20, 4354–4357
  • "Dibenzofuran Synthesis: Decarbonylative Intramolecular C‐H Arylation of Aromatic Esters"
    Okita, T.; Komatsuda, M.; Saito, A. N,; Hisada, T.; Takahara, T. T.; Nakayama, K. P.; Isshiki, R.; Takise, R.; Muto, K.; Yamaguchi, J.*
    Asian J. Org. Chem., 2018, 7, 1358-1361
  • " Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst"
    Okita, T.; Muto, K.; Yamaguchi, J.*
    Org. Lett, 2018, 20, 3132-3135
  • "Pd‐Catalyzed Decarbonylative C‐H Coupling of Azoles and Aromatic Esters"
    Matsushita, K.; Takise, R.; Hisada, T.; Suzuki, S.; Isshiki, R.; Itami, K.; Muto, K.; Yamaguchi, J.*
    Chem Asian. J., 2018, 13, 2393-2396
  • "Decarbonylative Aryl Thioether Synthesis by Ni Catalysis"
    Ishitobi, K.; Isshiki, R.; Asahara, K. K.; Lim, C.; Muto, K.; Yamaguchi, J.*
    Chem. Lett., 2018, 47, 756-759
  • "Decarbonylative C_P Bond Formation using Aromatic Esters and Organophosphorus Compounds"
    Issiki, R.; Muto, K.; Yamaguchi, J.*
    Org. Lett., 2018, vo.20, pp. 1150-1153
  • "Catalytic α-Arylation of Ketones with Heteroaromatic Esters"
    Isshiki, R.; Takise, R.; Itami, K.; Muto, K.; Yamaguchi, J.
    Synlett, 2017, vo.28, pp. 2599-2603
  • "Synthesis of Octaaryl Naphthalenes and Anthracenes with Different Substituents"
    Suzuki, S.; Itami, K.; Yamaguchi, J.
    Angew. Chem., Int. Ed., 2017, vo.56, pp. 15010-15013
  • "Rh-Catalyzed Regiodivergent Hydrosilylation of Acyl aminocyclopropanes Controlled by Monophosphine Ligands"
    Kondo, H.: Itami, K.; Yamaguchi, J.
    Chem Sci., 2017, vo.8, pp. 3799-3803
  • "Theoretical Elucidation of Potential Enantioselectivity in a Pd-Catalyzed Aromatic C-H Coupling Reaction"
    Nishimoto,Y.;_Kondo, H.;_Yamaguchi, K.;_Yokogawa, D.;_Yamaguchi, J.;_Itami, K.;_Irle, S.;_
    J. Org. Chem._, 2017,4,11, vo.82, pp. 4900-4906
  • "Synthesis of Multiply Arylated Pyridines"
    Asako, T.; Hayashi, W.; Suzuki, S.; Amaike, K.; Itami, K.; Muto, K.; Yamaguchi, J.
    Tetrahedron, 2017,4,2, vo.73, pp. 3669-3676
  • "Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis"
    Takise, R.; Isshiki, R. Muto K.; Itami, K.; Yamaguchi, J.
    J. Am. Chem. Soc., 2017, 139, 3340–3343
  • "Structure-Activity Relation of AMOR Sugar Molecule thatActivates Pollen-Tubes for Ovular Guidance"
    Jiao J.; Mizukami, A.G.; Sankaranarayanan, S.; Yamaguchi, J.; Itami, K.; Higashiyama, T.
    Plant Physiol., 2017, 173, 354–363
  • " Palladium-Catalyzed Decarbonylative Alkynylation of Aromatic Esters"
    Okita, T.; Kumazawa, K.; Takise, R.; Muto, K.; Itami, K.; Yamaguchi, J.
    Chem Lett., 2017, 46, 218–220.
  • "Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids"
    Muto, K.; Hatakeyama, T.; Itami, K; Yamaguchi, J.
    Org. Lett., 2016, 18, 5106–5109
  • " C-H Activation Enables Rapid Structure-Activity Relationship Study of Arylcylclopropyl amines for Potent and Selective LSD1 Inhibitors"
    Miyamura, S.; Araki, M; Ota, Y; Itoh, Y; Yasuda, S; Masada, M; Taniguchi, T,; Sowa, Y; Sakai, T; Suzuki, T; Itami, K.; Yamaguchi, J
    Org. Biomol. Chem., 2016, 14, 8576–8585.
  • "Cyanation of Phenol Derivatives with Aminoacetonitriles by Nickel Catalysis"
    Takise, R; Itami, K; Yamaguchi, J.
    Org. Lett., 2016, 18, 4428–4431

Review

  • 「Cross-coupling of Aromatic Esters and Amides」 Takise, R.; Muto, K.; Yamaguchi, J.*, Chem. Soc. Rev., 46, 5864-5888, 2017
  • 「Synthesis of Fully Arylated (Hetero)arenes」 Suzuki, S.; Yamaguchi. J., Chem. Commun., 53, 1568–1582., 2017
  • 「Toward an Ideal Synthesis of (Bio)molecules through Direct Arene Assembling Reactions」 Yamaguchi, J.; Itami, K., Bull. Chem. Soc. Jpn., 90, 367–383, 2017
  • 「Syntheses of Biologically Active 2-Arylcyclopropylamines」 Miyamura, S.; Itami, K.; Yamaguchi, J, Synthesis, 49, 1131–1149, 2017

Conference

  • UC Berkley
    "Making bonds by breaking bonds: An unconventional approach to making molecules", Invited Lecture
    Yamaguchi, J.
    12/3/2018~12/3/2020, Berkley, USA
  • The 19th OMCOS
    "Development of Catalytic Decarbonylative Coupling of Aromatic Esters", Poster Presentation
    Kei Muto,Ryosuke Takise, Ryota Isshiki, Toshimasa Okita, Kazushi Kumazawa, Kenichiro Itami, Junichiro Yamaguchi
    6/28/2017~6/28/2017, ICC Jeju, Korea
  • Boston University
    "Aromatic Molecules: Decarbonylative Coupling and Multiple Arylation", Invited Lecture
    YAMAGUCHI, Junichiro
    6/27/2017~6/27/2017, Boston, USA
  • Boston College
    "Aromatic Molecules: Decarbonylative Coupling and Multiple Arylation", Invited Lecture
    YAMAGUCHI, Junichiro
    6/26/2017~6/26/2017, Boston, USA
  • Gordon Research Conference "Heterocyclic Compounds"
    "Decarbonylative transformation of aromatic esters and multi-arylation of arenes", Invited Lecture
    YAMAGUCHI, Junichiro
    6/19/2017~6/19/2017, Newport, USA
  • ISPAC 2017
    "Synthesis of Fully Arylated Arenes, Acenes, and Benzoheteroles", Keynote Lecture
    YAMAGUCHI, Junichiro
    6/9/2017~6/9/2017, Viet Nam, Viet Nam

National Conference

  • 第50回有機金属若手の会夏の学校
    "パラジウム触媒による芳香族エステルの脱カルボニル型アルキニル化反応", ポスター発表
    大北俊将・熊澤一将・瀧瀬瞭介・武藤慶・伊丹健一郎・山口潤一郎
    8/8/2017~8/8/2017, 北海道
  • 第49回若手ペプチド夏の勉強会
    "マルチアリールピリジン構築法とチオペプチド抗生物質への応用", 口頭発表
    浅子貴士・武藤慶・山口潤一郎
    8/6/2017~8/6/2017, 長崎
  • 先進研究講演会
    "芳香族分子の新奇カップリング法・合成法の開発", 招待講演
    山口潤一郎
    4/22/2017~4/22/2017, 東京

Award

  • 「早稲田大学リサーチアワード(国際研究発信力)」
    受賞者:山口潤一郎
    贈呈元:早稲田大学
    受賞日:1/27/2020
  • 「第42回化学教育賞」
    受賞者:山口潤一郎
    贈呈元:日本化学会
    受賞日:3/21/2018
  • 「科学技術への顕著な貢献 2017(ナイスステップな研究者)」
    受賞者:山口潤一郎
    贈呈元:科学技術・学術政策研究所
    受賞日:12/26/2017
  • 「FACS Distinguished Young Chemist Award 2017 in Organic Chemistry」
    受賞者:Junichiro Yamaguchi
    贈呈元:Federation of Asian Chemical Societies
    受賞日:4/2017

Media

  • c2W, その他
    「Kat maakt ethers door esters te snoeien」
    Takise, R.; Isshiki, R. Muto K.; Itami, K.; Yamaguchi, J. , 3/7/2017
  • Phys.org, その他
    「Revolutionary process to create ether from esters using metal catalysts」
    Takise, R.; Isshiki, R. Muto K.; Itami, K.; Yamaguchi, J. , 3/6/2017
  • 日経産業新聞, 新聞
    「抗がん剤に使う有機物、安価に合成できる触媒、早大・名大が共同開発」
    Takise, R.; Isshiki, R. Muto K.; Itami, K.; Yamaguchi, J., 2/27/2017
    PDF File
  • 化学工業日報, 新聞
    「ジアリールエーテル骨格、早大、新触媒用いエステルから合成」
    Takise, R.; Isshiki, R. Muto K.; Itami, K.; Yamaguchi, J., 2/25/2017
    PDF File