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C(sp3)-H functionalization of organosulfur compounds powered by novel directing group

Research Project

Project/Area Number 18K14212
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionKyoto University

Principal Investigator

Nogi Keisuke  京都大学, 理学研究科, 助教 (60779148)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2018: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
KeywordsC-H官能基化 / C-H結合官能基化 / パラジウム触媒 / 配向基 / スルホキシド / ヨウ素化 / アルコキシ化 / 遷移金属触媒 / スルフィミド / C(sp3)-H官能基化
Outline of Final Research Achievements

C(sp3)-H functionalization of organosulfur compounds by means of sulfimides bearing nitrogen-coordinating unit has been investigated. During the investigation, we found that sulfoxide directing group promotes C-H iodination and alkoxylation of aromatic compounds. Especially, the peri-C-H bonds of π-extended aromatic compounds could be selectively converted to afford the corresponding multifunctionalized molecules.

Academic Significance and Societal Importance of the Research Achievements

炭素-水素(C-H)結合は有機化合物中に普遍的に存在し、それを事前修飾を必要とすることなく直接官能基化することができれば工程数や廃棄物の削減に繋がると期待される。本研究では硫黄を含む有機化合物のC-H結合官能基化を目指し、複数の新反応を開発した。有機硫黄化合物は入手も容易であり、また生成物中に残された硫黄部位はさらに変換することも可能であることから、有機合成化学にさらなる進展をもたらしうると期待できる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (49 results)

All 2020 2019 2018 Other

All Int'l Joint Research (1 results) Journal Article (19 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 19 results,  Open Access: 1 results) Presentation (28 results) (of which Int'l Joint Research: 13 results) Remarks (1 results)

  • [Int'l Joint Research] コロンビア大学(米国)

    • Related Report
      2018 Research-status Report
  • [Journal Article] Palladium‐Catalyzed peri‐Selective C-H Fluoroalkoxylation of Aryl Sulfoxides2020

    • Author(s)
      Sato Tomohiko、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      ChemCatChem

      Volume: 12 Issue: 13 Pages: 3467-3471

    • DOI

      10.1002/cctc.202000485

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium‐Catalyzed C-H Iodination of Arenes by Means of Sulfinyl Directing Groups2020

    • Author(s)
      Saito Hayate、Yamamoto Keita、Sumiya Yosuke、Liu Ling‐Jun、Nogi Keisuke、Maeda Satoshi、Yorimitsu Hideki
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 15 Issue: 16 Pages: 2442-2446

    • DOI

      10.1002/asia.202000591

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles2020

    • Author(s)
      Fukazawa Mizuki、Takahashi Fumiya、Nogi Keisuke、Sasamori Takahiro、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 6 Pages: 2303-2307

    • DOI

      10.1021/acs.orglett.0c00490

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ni-Catalyzed Carboxylation of C(sp2)?S Bonds with CO2: Evidence for the Multifaceted Role of Zn2020

    • Author(s)
      Yanagi Tomoyuki、Somerville Rosie J.、Nogi Keisuke、Martin Ruben、Yorimitsu Hideki
    • Journal Title

      ACS Catalysis

      Volume: 10 Issue: 3 Pages: 2117-2123

    • DOI

      10.1021/acscatal.9b05141

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Sulfoxide-Directed Iterative Assembly into Oligoarenes2019

    • Author(s)
      Yanagi Tomoyuki、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Synlett

      Volume: 印刷中 Issue: 02 Pages: 153-157

    • DOI

      10.1055/s-0037-1611767

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Construction of Biaryls from Aryl Sulfoxides and Anilines by Means of a Sigmatropic Rearrangement2019

    • Author(s)
      Yanagi Tomoyuki、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Chemistry A European Journal

      Volume: 26 Issue: 4 Pages: 783-787

    • DOI

      10.1002/chem.201903570

    • NAID

      120006800745

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cross-Coupling of Aryl Trifluoromethyl Sulfones with Arylboronates by Cooperative Palladium/Rhodium Catalysis2019

    • Author(s)
      Fukuda Jun-ichi、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 22 Pages: 8987-8991

    • DOI

      10.1021/acs.orglett.9b03393

    • NAID

      120006800717

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Arylthiolation of Alkynes Enabled by Surmounting Competitive Dimerization of Alkynes2019

    • Author(s)
      Uno Daisuke、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 20 Pages: 8295-8299

    • DOI

      10.1021/acs.orglett.9b03056

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Diborative Reduction of Alkynes to 1,2-Diboryl-1,2-Dimetalloalkanes: Its Application for the Synthesis of Diverse 1,2-Bis(boronate)s2019

    • Author(s)
      Takahashi Fumiya、Nogi Keisuke、Sasamori Takahiro、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 12 Pages: 4739-4744

    • DOI

      10.1021/acs.orglett.9b01622

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Alkoxycarbonylation of Arylsulfoniums2019

    • Author(s)
      Minami Hiroko、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 8 Pages: 2518-2522

    • DOI

      10.1021/acs.orglett.9b00067

    • NAID

      120006621582

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Annulative Synthesis of Benzofurans from General Alkenyl Sulfoxides and Phenols via Pummerer/Sigmatropic Cascade2019

    • Author(s)
      Hori Mitsuki、Yanagi Tomoyuki、Murakami Kei、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 92 Issue: 2 Pages: 302-311

    • DOI

      10.1246/bcsj.20180321

    • NAID

      130007593735

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photoredox-Catalyzed Alkenylation of Benzylsulfonium Salts2019

    • Author(s)
      Otsuka Shinya、Nogi Keisuke、Rovis Tomislav、Yorimitsu Hideki
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 14 Issue: 4 Pages: 532-536

    • DOI

      10.1002/asia.201801732

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Palladium‐Catalyzed Insertion of Isocyanides into the C‐S Bonds of Heteroaryl Sulfides2018

    • Author(s)
      Otsuka Shinya、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Angewandte Chemie - International Edition

      Volume: 印刷中 Issue: 22 Pages: 6653-6657

    • DOI

      10.1002/anie.201802369

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Mizoroki-Heck-Type Alkenylation of Monoaryldialkylsulfoniums2018

    • Author(s)
      Uno Daisuke、Minami Hiroko、Otsuka Shinya、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 13 Issue: 17 Pages: 2397-2400

    • DOI

      10.1002/asia.201800489

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Ring-Opening Silylation of Benzofurans with Disilane2018

    • Author(s)
      Saito Hayate、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 34 Pages: 11030-11034

    • DOI

      10.1002/anie.201806237

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Reduction of Aryl Sulfones to Arenes by Means of Alkylmagnesium Reagents2018

    • Author(s)
      Fukuda Jun-ichi、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 7 Issue: 10 Pages: 2049-2052

    • DOI

      10.1002/ajoc.201800473

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Sigmatropic Dearomatization/Defluorination Strategy for C-F Transformation: Synthesis of Fluorinated Benzofurans from Polyfluorophenols2018

    • Author(s)
      Okamoto Koichi、Hori Mitsuki、Yanagi Tomoyuki、Murakami Kei、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 43 Pages: 14230-14234

    • DOI

      10.1002/anie.201809035

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Desulfitative Coupling: Nickel-Catalyzed Transformation of Diaryl Sulfones into Biaryls via Extrusion of SO22018

    • Author(s)
      Takahashi Fumiya、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 20 Pages: 6601-6605

    • DOI

      10.1021/acs.orglett.8b02972

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Recent development of ortho -C?H functionalization of aryl sulfoxides through [3,3] sigmatropic rearrangement2018

    • Author(s)
      Yanagi Tomoyuki、Nogi Keisuke、Yorimitsu Hideki
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 31 Pages: 2951-2959

    • DOI

      10.1016/j.tetlet.2018.06.055

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Seven-membered Dialkoxysilyl Group Activatable under Specific Conditions2020

    • Author(s)
      Hayate Saito, Jun Shimokawa, Hideki Yorimitsu
    • Organizer
      Nanyang Research Conference on Synthetic Chemistry and Catalysis
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] アリールスルホキシドとフェノールの脱水素カップリング反応に関する機構解析2020

    • Author(s)
      柳智征・野木馨介・依光英樹
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] [3,3] シグマトロピー転位を利用したケテンジチオアセタールモノオキシドとN-スルホニルアニリンからのインドール合成2020

    • Author(s)
      木下純・吉田陽・岡本浩一・柳智征・野木馨介・依光英樹
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Methylsulfanyl group: multipotent directing group for palladium-catalyzed C_H iodination of arenes2019

    • Author(s)
      Keisuke Nogi, Keita Yamamoto, Ling-Jun Liu, Hideki Yorimitsu
    • Organizer
      The 47th Naito Conference on C_C Bond Activation and Transformation
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] アリールスルホキシドとアニリン誘導体を用いた[3,3]シグマトロピー転位によるビアリール合成2019

    • Author(s)
      吉田陽、岡本浩一、柳智征、野木馨介、依光英樹
    • Organizer
      第36回有機合成化学セミナー
    • Related Report
      2019 Research-status Report
  • [Presentation] パラジウム触媒を用いたアリールスルホキシドのC-Hアルコキシ化2019

    • Author(s)
      佐藤友彦・野木馨介・依光英樹
    • Organizer
      第36回有機合成化学セミナー
    • Related Report
      2019 Research-status Report
  • [Presentation] パラジウム触媒を用いたアリールスルホキシドのC-Hアルコキシ化2019

    • Author(s)
      佐藤友彦・野木馨介・依光英樹
    • Organizer
      第66回有機金属化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] アリールスルホキシドとフェノールの脱水素カップリング反応に関する機構解析2019

    • Author(s)
      柳智征・野木馨介・依光英樹
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] アリールスルホキシドとアニリン誘導体を用いた[3,3]シグマトロピー転位によるビアリール合成2019

    • Author(s)
      吉田陽、岡本浩一、柳智征、野木馨介、依光英樹
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] パラジウム触媒を用いたヘテロアリールスルフィドの炭素―硫黄結合へのアルキン挿入2019

    • Author(s)
      宇野大介・野木馨介・依光英樹
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ニッケル触媒による二酸化炭素を用いたアリールスルホニウムのカルボキシル化2019

    • Author(s)
      柳智征・野木馨介・依光英樹
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of Thioesters through Palladium-Catalyzed Insertion of Isocyanides into Heteroaryl Sulfides2018

    • Author(s)
      Shinya Otsuka, Keisuke Nogi, Hideki Yorimitsu
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Cobalt-Catalyzed Reduction of Aryl Sulfones to Arenes by Means of Alkylmagnesium Reagents2018

    • Author(s)
      Jun-ichi Fukuda, Keisuke Nogi, Hideki Yorimitsu
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Pd-Catalyzed Borylation of Arylsulfonium Salts with Diborons2018

    • Author(s)
      Hiroko Minami, Shinya Otsuka, Keisuke Nogi Hideki Yorimitsu
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Ring-opening Silylation of Benzofurans with a Disilane2018

    • Author(s)
      Hayate Saito, Keisuke Nogi, Hideki Yorimitsu
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Nickel-Catalyzed Desulfonylative Transformation of Diaryl Sulfones into Biaryls2018

    • Author(s)
      Fumiya Takahashi, Keisuke Nogi, Hideki Yorimitsu
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Palladium-Catalyzed Mizoroki-Heck-Type Alkenylation of Monoaryldialkylsulfoniums2018

    • Author(s)
      Daisuke Uno, Hiroko Minami, Shinya Otsuka, Keisuke Nogi, Hideki Yorimitsu
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] ニッケル触媒を用いた脱亜硫酸を伴うジアリールスルホンのビアリールへの変換2018

    • Author(s)
      高橋郁也・野木馨介・依光英樹
    • Organizer
      第7回JACI/GSCシンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] パラジウム触媒を用いたアリールスルホニウムの溝呂木・ヘック反応2018

    • Author(s)
      宇野大介・南裕子・大塚慎也・野木馨介・依光英樹
    • Organizer
      第7回JACI/GSCシンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] ニッケル触媒を用いた脱亜硫酸を伴うジアリールスルホンのビアリールへの変換2018

    • Author(s)
      高橋郁也・野木馨介・依光英樹
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] パラジウム触媒を用いたアリールスルホニウムの溝呂木・ヘック反応2018

    • Author(s)
      宇野大介・南裕子・大塚慎也・野木馨介・依光英樹
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジシランを用いた銅触媒によるベンゾフラン類の開環シリル化反応2018

    • Author(s)
      齊藤颯・ 野木馨介・ 依光英樹
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Ring-opening Silylation of Benzofurans with a Disilane2018

    • Author(s)
      Hayate Saito, Keisuke Nogi, Hideki Yorimitsu
    • Organizer
      14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Nickel-Catalyzed Desulfonylative Transformation of Diaryl Sulfones into Biaryls2018

    • Author(s)
      Fumiya Takahashi, Keisuke Nogi, and Hideki Yorimitsu
    • Organizer
      14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Palladium-Catalyzed Mizoroki-Heck Reaction of Arylsulfoniums2018

    • Author(s)
      Daisuke Uno, Hiroko Minami, Shinya Otsuka, Keisuke Nogi, Hideki Yorimitsu
    • Organizer
      14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Methylsulfinyl Group: Multipotent Directing Group for Palladium-Catalyzed C-H Iodination of Arenes2018

    • Author(s)
      Keisuke Nogi, Keita Yamamoto, Ling-Jun Liu, Hideki Yorimitsu
    • Organizer
      28th International Symposium on the Organic Chemistry of Sulfur (ISOCS-28)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Methylsulfinyl Group: Modifiable Directing Group for Palladium-Catalyzed C-H Iodination of Arenes2018

    • Author(s)
      Keisuke Nogi, Keita Yamamoto, Ling-Jun Liu, Hideki Yorimitsu
    • Organizer
      4th International Symposium on C_H Activation (ISCHA-3)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 変換可能なスルフィニル配向基を利用した アリールスルホキシドの触媒的C-Hヨウ素化2018

    • Author(s)
      野木馨介・山本啓太・大塚慎也・依光英樹
    • Organizer
      第113回有機合成シンポジウム
    • Related Report
      2018 Research-status Report
  • [Remarks] 研究室HP

    • URL

      http://kuchem.kyoto-u.ac.jp/orgchem/yorimitsu_lab/index.html

    • Related Report
      2018 Research-status Report

URL: 

Published: 2018-04-23   Modified: 2022-01-27  

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