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

Shigeki Matsunaga » Japanese

Affiliation Faculty of Pharmaceutical Sciences, Hokkaido University
Position Professor
Contact Email
HP http://www.pharm.hokudai.ac.jp/yakuzou/member_e.html
Speciality Synthetic Organic Chemistry, Asymmetric Catalysis
Keyword asymmetric catalysis, asymmetric synthesis, transition metal catalysis, C-H functionalization
Institute The Pharmaceutical Society of Japan, The Chemical Society of Japan, The Society of Synthetic Organic Chemistry Japan, The Japanese Society for Process Chemistry, The Kinki Chemical Society Japan, The Rare Earth Society of Japan, American Chemical Society

Abstract

◆Research Topics:
Design of Catalytically Active Sites for Multi-Centers Control and their Application to Organic Transformation

Achievement

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Original papers

  • "Cp*CoIII/Chiral Carboxylic Acid-Catalyzed Enantioselective 1,4-Addition Reactions of Indoles to Maleimides"
    Kurihara, T.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Asian J. Org. Chem., 2020, 9, 368-371
  • "Catalytic Enantioselective Methylene C(sp3)–H Amidation of 8-Alkylquinolines Using Cp*RhIII/Chiral Carboxylic Acid System"
    Fukagawa, S.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Angew. Chem., Int. Ed. , 2019, 58, 18154-18158
  • "Imidate as the Intact Directing Group for the Cobalt-Catalyzed C–H Allylation"
    Tanaka, R.; Tanimoto, I.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    J. Org. Chem., 2019, 84, 13203-13210
  • "Chiral 2-Aryl Ferrocene Carboxylic Acids for the Catalytic Asymmetric C(sp3)–H Activation of Thioamides"
    Sekine, D.; Ikeda, K.; Fukagawa, S.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Organometallics, 2019, 38, 3921-3926
  • "Cobalt-catalyzed Synthesis of Homoallylic Amines from Imines and Terminal Alkenes"
    Tanaka, R.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Chem. Lett., 2019, 48, 1046-1049
  • "C–H γ,γ,γ-Trifluoroalkylation of Quinolines via Visible-Light-Induced Sequential Radical Additions"
    Kumagai, Y.; Murakami, N.; Kamiyama, F.; Tanaka, R.; *Yoshino, T.; *Kojima, M.; *Matsunaga, S.
    Org. Lett., 2019, 21, 3600-3605
  • "Synthesis of Heteroaryl Iodanes(III) via ipso-Substitution Reactions Using Iodine Triacetate Assisted by HFIP"
    Matsuoka, K.; Komami, N.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Asian J. Org. Chem., 2019, 8, 1107-1110
  • "Cobalt-Catalyzed Allylic Alkylation Enabled by Organophotoredox Catalysis"
    Takizawa, K.; Sekino, T.; Sato, S.; Yoshino, T.; *Kojima, M.; *Matsunaga, S.
    Angew. Chem., Int. Ed. , 2019, 58, 9199-9203
  • "Synthesis of 1,1’-Spirobiindane-7,7’-disulfonic Acid and Disulfonimide: Application for Catalytic Asymmetric Aminalization"
    Kurihara, T.; Satake, S.; Hatano, M.; Ishihara, K.; *Yoshiko, T.; *Matsunaga, S.
    Chem. Asian J. , 2018, 13(17), 2378–2381
  • "One-Step Synthesis of 4H-3,1-Benzoxazin-4-ones from Weinreb Amides and 1,4,2-Dioxazol-5-ones via Cobalt-Catalyzed C-H Bond Activation"
    Tanimoto, I.; Kawai, K.; Sato, A.; *Yoshino, T.; *Matsunaga, S.
    Heterocycles, 2019, 99, 118-125
  • "Synthesis of Functionalized Monoaryl‐λ3‐iodanes through Chemo‐ and Site‐selective ipso‐Substitution Reactions"
    Komami, N.; Matsuoka, K.; Nakano, A.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Chem. Eur. J., 2019, 25(5), 1217-1220
  • "Enantioselective C(sp3)–H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System"
    Fukagawa, S.; Kato, Y.; Tanaka, R.; Kojima, M.; *Yoshino, T.; *Matsunaga, S.
    Angew. Chem. Int. Ed., 2019, 58(4), 1153-1157
  • "Chiral Carboxylic Acid‐Enabled Achiral Rhodium(III)-Catalyzed Enantioselective C−H Functionalization"
    Lin, L.; Fukagawa, S.; Sekine, D.; Tomita, E.; *Yoshino, T.; *Matsunaga, S.
    Angew. Chem. Int. Ed., 2018, 57(37), 12408-12052
  • "Pentamethylcyclopentadienyl Rhodium(III)-Chiral Disulfonate Hybrid Catalysis for Enantioselective C-H Bond Functionalization"
    Satake, S.; Kurihara, T.; Nishikawa, K.; Mochizuki, T.; Hatano, M.; Ishihara, K.; *Yoshino, T.; *Matsunaga, S.
    Nat. Catal., 2018, 1(8), 585-591
  • "5-((3-Bromoallyl)Sulfonyl)-1H-Tetrazoles for Bromodiene Synthesis"
    Suzuki, T.; Fukagawa, S.; Yoshino, T.; Anada, M.; *Matsunaga, S.
    Heterocycles, 2018, 97(2), 1304-1312
  • "Weinreb Amide Directed Versatile C-H Bond Functionalization under (η5-Pentamethylcyclopentadienyl)cobalt(III) Catalysis"
    Kawai, K.; Bunno, Y.; *Yoshino, T.; *Matsunaga, S.
    Chem. Eur. J., 2018, 24(40), 10231-10237
  • "Synthesis of 1,1'-Spirobiindane-7,7'-Disulfonic Acid and Disulfonimide: Application for Catalytic Asymmetric Aminalization"
    Kurihara, T.; Satake, S.; Hatano, M.; Ishihara K.; *Yoshino T.; *Matsunaga, S.
    Chem. Asian J., 2018, 13(17), 2378-2381
  • "Palladium-Catalyzed Germylation of Aryl Bromides and Aryl Triflates Using Hexamethyldigermane"
    Komami, N.; Matsuoka, K.; Yoshino, T.; Matsunaga S.
    Synthesis, 2018, 50(10), 2067-2075
  • "Synthesis of Fluorine-Containing 6-Arylpurine Derivatives via Cp*Co(III)-Catalyzed C–H Bond Activation"
    Murakami, N.; Yoshida, M.; Yoshino, T.; Matsunaga S.
    Chem. Pharm. Bull., 2018, 66, 51-54
  • "CATALYTIC ENANTIOSELECTIVE DESYMMETRIZATION OF MESO-AZIRIDINES WITH FLUOROMALONATES"
    Fukagawa, S.; Xu, Y.; Anada, M.; Yoshino, T.; Matsunaga, S.
    Heterocycles, 2017, 94, 1337-1350
  • "Cp*CoIII-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines"
    Yoshida, M.; Kawai, K.; Tanaka, R.; Yoshino, T.; Matsunaga, S.
    Chem. Commun., 2017, 53, 5974-5977
  • "Stereoselective Synthesis of Tetrasubstituted Alkenes via Cp*CoIII-Catalyzed C-H Alkenylation/Directing Group Migration Sequence"
    Ikemoto, H.; Tanaka, R.; Sakata, K.; Kanai, M.; Yoshino, T.; Matsunaga, S.
    Angew. Chem. Int. Ed., 2017, 56, 7156-7160
  • "Diastereo- and Enantioselective Construction of 6,7-Dioxabicyclo[2.2.1]heptane Derivatives by a Dirhodium(II)-Catalyzed Intramolecular C-H Insertion Reaction"
    Miyazawa, T.; Imai, K.; Ito, M.; Takeda, K.; Anada, M.; Matsunaga, S.; Hashimoto, S.
    Heterocycles, 2017, 95, 1211-1229
  • "Site- and Regioselective Monoalkenylation of Pyrroles with Alkynes via Cp*CoIII Catalysis"
    Tanaka, R.; Ikemoto, H.; Kanai, M.; Yoshino, T.; Matsunaga, S.
    Org. Lett., 2016, 18, 5732-5735
  • "Cp*CoIII-Catalyzed Dehydrative C–H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols"
    Bunno, Y.; Murakami, N.; Suzuki, Y.; Kanai, M.; Yoshino, T.; Matsunaga, S.
    Org. Lett., 2016, 18, 2216-2219
  • "Catalytic Asymmetric Iterative/Domino Aldehyde Cross-Aldol Reactions for the Rapid and Flexible Synthesis of 1,3-Polyols"
    Lin, L.; Yamamoto, K.; Mitsunuma, H.; Kanzaki, Y.; Matsunaga, S.; Kanai, M.
    J. Am. Chem. Soc., 2015, 137, 15418-15421
  • "Cp*CoIII Catalyzed Site-Selective C-H Activation of Unsymmetrical O-Acyl Oximes: Synthesis of Multisubstituted Isoquinolines from Terminal and Internal Alkynes"
    Sun, B.; Yoshino, T.; Kanai, M.; Matsunaga, S.
    Angew. Chem., Int. Ed., 2015, 54, 12968-12972

Review

  • 「Diverse Approaches for Enantioselective C–H Functionalization Reactions Using Group 9 CpxMIII Catalysts」 *Yoshino, T.; Satake, S.; *Matsunaga, S., Chem. Eur. J., 26, Early View, 2020
  • 「Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources」 *Yoshino, T.; *Matsunaga, S., Synlett, 30, 1384-1400, 2019
  • 「High-Valent Cobalt-Catalyzed C-H Bond Functionalization」 Yoshino T.; Matsunaga S., Advances in Organometallic Chemistry, 68, 197-247, 2017
  • 「(Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed C–H Bond Functionalization: From Discovery to Unique Reactivity and Selectivity」 Yoshino, T.; Matsunaga, S., Adv. Synth. Catal., 359, 1245-1262, 2017

Conference

  • Strasbourg-Hokkaido Symposium
    "Chiral Acid-Enabled Achiral Rh(III)&Co(III)-Catalyzed Asymmetric C-H Bond Functionalization ", Invited Lecture
    *Matsunaga, S.
    11/18/2019~11/19/2019, Strasbourg, France
  • ICCEOCA-14
    "Synthesis of Functionalized Monoaryl Iodanes(III) via ipso-Substitution Reactions", Poster Presentation
    *Matsunaga, S.; Matsuoka, K.; Komami, N.; Nakano, A.; Kojima, M.; Yoshino, T.
    9/26/2019~9/29/2019, Niseko, Japan
  • The 47th Naito Conference C–H Bond Activation and Transformation
    "Chiral Acid-Enabled Achiral Rh(III)&Co(III)-Catalyzed Asymmetric C-H Bond Functionalization", Invited Lecture
    *Matsunaga, S.
    7/2/2019~7/5/2019, Sapporo, Japan
  • International Conference on Organometallics and Catalysis (2018), ICOC-2018
    "Chiral Acid-Enabled Achiral Rh(III)&Co(III)-Catalyzed Asymmetric C-H Bond Functionalization", Invited Lecture
    *Matsunaga, S.
    12/13/2018~12/16/2018, Goa, India
  • Lecture at Indian Institute of Technology, Kanpur
    "Chiral Acid-Enabled Achiral Rh(III)&Co(III)-Catalyzed Asymmetric C-H Bond Functionalization", Invited Lecture
    *Matsunaga, S.
    12/12/2018~12/12/2018, Kanpur, India
  • Lecture at Indian Institute of Technology, Delhi
    "Chiral Acid-Enabled Achiral Rh(III)&Co(III)-Catalyzed Asymmetric C-H Bond Functionalization", Invited Lecture
    *Matsunaga, S.
    12/10/2018~12/10/2018, Delhi, India
  • 13th International Conference on Cutting-Edge Organic Chemistry in Asian
    "Chiral Acid-Enabled Achiral Rh(III)&Co(III)-Catalyzed Asymmetric C-H Bond Functionalization", Invited Lecture
    *Matsunaga, S.
    11/1/2018~11/4/2018, Bangkok, Thailand
  • 4th Internatiol Symposium on C-H Activation
    "Unique Reactivity and Selectivity of Cp*Co(III) Catalysis in C-H Activation", Invited Lecture
    *Matsunaga, S.
    8/30/2018~9/2/2018, Hiyoshi, Japan
  • 1st Sino-Japanese Symposium on Catalysis for Precision Synthesis
    "The Unique Reactivity and Selectivity of Cp*Co(III) Catalysis in C-H Activation", Invited Lecture
    *Matsunaga, S
    5/27/2018~5/30/2018, Shanghai, China
  • Singapore Japan Germany Trilateral Symposium on PrecisionSynthesis & Catalysis
    "Unique Reactivity and Selectivity of Cp*Co(III) Catalysis in C-H Bond Functionalization", Invited Lecture
    Matsunaga, S.
    11/19/2017~11/21/2017, Singapore, Singapore
  • 第2回精密制御反応場国際シンポジウム
    "Catalytic Asymmetric Total Synthesis of Frondosin A Under Precisely Designed Dinuclear Rh-Catalysis", Poster Presentation
    Takizawa, K.; Sunadoi, Y.; Anada, M.; Hashimoto, S.; Matsunaga, S.
    5/26/2017~5/27/2017, 大阪, 日本
  • 19th HU-SNU Joint Symposium on New Frontiers on Chemical Pharmaceutical Sciences
    "Cationic Cp*Co(III) Catalysis for C-H Bond Functionalization", Invited Lecture
    Matsunaga, S.
    11/24/2016~11/24/2016, Sapporo, Japan
  • 4th Lower Saxonian Catalysis Symposium
    "Cationic Cp*Co(III) Catalysis for C-H Bond Functionalization", Keynote Lecture
    Matsunaga, S.
    9/19/2016~9/20/2016, Braunschweig, Germany
  • 3rd International Conference on Organometallics and catalysis (OM & Cat 2016)
    "Cationic Cp*Co(III) Catalysis for C-H Bond Functionalization", Invited Lecture
    Matsunaga, S.
    8/28/2016~8/30/2016, Seoul, Korea
  • Lecture at Pusan National University
    "First-Row Transition Metal Catalysis for Atom-Efficient Organic Synthesis ~Dinuclear Schiff Base Asymmetric Catalysis & Cationic Cp*Co(III) Catalysis~", Invited Lecture
    Matsunaga, S.
    5/25/2016~5/25/2016, Busan, Korea
  • Lecture at Chungbuk National University
    "First-Row Transition Metal Catalysis for Atom-Efficient Organic Synthesis ~Dinuclear Schiff Base Asymmetric Catalysis & Cationic Cp*Co(III) Catalysis~", Invited Lecture
    Matsunaga, S.
    5/24/2016~5/24/2016, Chungbuk, Korea
  • Lecture at Seoul National University
    "First-Row Transition Metal Catalysis for Atom-Efficient Organic Synthesis ~Dinuclear Schiff Base Asymmetric Catalysis & Cationic Cp*Co(III) Catalysis~", Invited Lecture
    Matsunaga, S.
    5/23/2016~5/23/2016, Seoul, Korea
  • 5th UK-Japanese Asymmetric Catalysis Symposium
    "Dinuclear Schiff Base Cooperative Asymmetric Catalysis", Invited Lecture
    Matsunaga, S.
    3/14/2016~3/15/2016, Manchester, UK
  • Tateshina Conference 2015
    "Cp*Co(III)-Catalysis for C-H Bond Functionalization", Poster Presentation
    Matsunaga, S.
    11/6/2015~11/7/2015, Tateshina, Japan
  • The 10th International Conference on Cutting-Edge Organic Chemsitry in Asia (ICCEOCA-10)
    "Cp*Co(III)-Catalysis for C-H Bond Functionalization", Poster Presentation
    Matsunaga, S.
    11/2/2015~11/5/2015, Kaosiung, Taiwan

National Conference

  • 精密制御反応場 第4回公開シンポジウム
    "精密立体制御を実現する反応活性点の構築と分子変換", 招待講演
    松永茂樹
    1/10/2018~1/11/2018, 東京
  • 日本化学会 第97春季年会 (2017)
    "スピロ化合物に対するモノクローナル抗体の作製", ポスター発表
    内田雅之、谷本郁、穴田仁洋、松永茂樹、山口浩靖
    3/16/2017~3/19/2017, 横浜(日吉)
  • 第2回公開シンポジウム
    "分子認識による反応場制御", 口頭発表
    山口浩靖
    1/25/2017~1/26/2017, 名古屋
  • 薬学シンポジウム2016有機化学の先進的ビジョン
    "第1列遷移金属触媒を駆使する精密有機合成", 招待講演
    Matsunaga, S.
    10/17/2016~10/17/2016, 金沢

Award

  • 「Mukaiyama Award 2020」
    受賞者:S. Matsunaga
    贈呈元:有機合成化学協会
    受賞日:9/2020
  • 「Asian CORE Program/Advanced Research Network Lectureship Award 2018, China」
    受賞者:Matsunaga, S.
    贈呈元:Asian CORE Program, China
    受賞日:11/4/2018
  • 「Asian CORE Program/Advanced Research Network Lectureship Award 2018, Singapore」
    受賞者:Matsunaga, S.
    贈呈元:Asian CORE Program, Singapore
    受賞日:11/4/2018
  • 「Negishi Award」
    受賞者:Matsunaga, S.
    贈呈元:JST
    受賞日:3/5/2018
  • 「4th Research Front Award」
    受賞者:Matsunaga, S.
    贈呈元:Clarivate Analytics, Japan (Thomson Reuter, Japan)
    受賞日:7/7/2016
  • 「Asian Core Program Lectureship Award 2015 (Thailand)」
    受賞者:Shigeki Matsunaga
    贈呈元:International Conference on Cutting-Edge Organic Chemistry in Asia
    受賞日:11/5/2015
  • 「Asian Core Program Lectureship Award 2015 (Korea)」
    受賞者:Shigeki Matsunaga
    贈呈元:International Conference on Cutting-Edge Organic Chemistry in Asia
    受賞日:11/5/2015

Media

  • Chem. Eur. J. 2020, Accepted Article. DOI: 10.1002/chem.201905417, カバーピクチャ
    「Diverse Approaches for Enantioselective C–H Functionalization Reactions Using Group 9 CpxMIII Catalysts」
    *Yoshino, T.; Satake, S.; *Matsunaga, S., 1/28/2020
    総説の表紙絵
    PDF File
  • Adv. Synth. Catal., カバーピクチャ
    「Treasure-Hunting Under Cp*Co Catalysis」
    Yoshino, Y.; Matsunaga, S., 5/2017
    PDF File
  • SYNFACTs, 雑誌記事
    「Copper -Catalyzed Asymmetric Cross-Aldol Reactions」
    Lin, L.; Yamamoto, K.; Mitsunuma, H.; Kanzaki, Y.; Matsunaga, S.; Kanai, M. , 3/2016
    Selected as SynFact of the month and a cover picture
    PDF File

conference _management

  • 「Hokkaido Summer Symposium 2019 on Catalysis for Organic Synthesis」
    国際会議, Organizer (Chair), 7/1/2019~7/2/2019, Sapporo, Japan
  • 「Hokkaido Summer Symposium 2019 on Catalysis for Organic Synthesis 」
    国際会議, Organizer (Chair), 7/1/2019~7/2/2019, Sapporo, Japan