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Generation of organometallic reagents through decarbonylation of esters

Research Project

Project/Area Number 16H06887
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

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

Research Collaborator YORIMITSU Hideki  京都大学, 大学院理学研究科, 教授
Otsuka Shinya  京都大学, 大学院理学研究科, 大学院生
Project Period (FY) 2016-08-26 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords遷移金属触媒 / 有機金属化合物 / 脱カルボニル / ホウ素化 / ニッケル / パラジウム / エステル / 亜鉛化 / ホウ素化反応 / 亜鉛化反応
Outline of Final Research Achievements

We investigated decarbonylative transformations of esters to organometallic species such as organoboron or zinc compounds. During the investigation, instead of the target transformations, we succeeded in development of C-S bond cleaving transformations of aryl sulfoxides including Negishi-type arylation, Sonogashira-type alkynylation, Buchwald-Hartwig-type amination, Miyaura-type borylation. C-S bonds are considered as “inert” bond as same as C-O bonds, and our results would afford important perceptions for further investigation of C-S bond cleaving transformations.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • Research Products

    (37 results)

All 2018 2017 2016 Other

All Journal Article (11 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results,  Open Access: 1 results,  Acknowledgement Compliant: 2 results) Presentation (24 results) (of which Int'l Joint Research: 6 results) Remarks (2 results)

  • [Journal Article] Palladium-Catalyzed Borylation of Aryl Sulfoniums with Diborons2018

    • Author(s)
      Hiroko Minami, Shinya Otsuka, Keisuke Nogi, and Hideki Yorimitsu
    • Journal Title

      ACS Catal.

      Volume: 8 Issue: 1 Pages: 579-583

    • DOI

      10.1021/acscatal.7b03841

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Amination of Aryl Sulfoxides2018

    • Author(s)
      Yuto Yoshida, Shinya Otsuka, Keisuke Nogi, and Hideki Yorimitsu
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 4 Pages: 1134-1137

    • DOI

      10.1021/acs.orglett.8b00060

    • NAID

      120006406842

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Double Borylation of Diaryl Sulfoxides with Diboron2017

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

      Synthesis

      Volume: 49 Issue: 21 Pages: 4769-4774

    • DOI

      10.1055/s-0036-1588848

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rh/Cu-cocatalyzed Ring-opening Diborylation of Dibenzothiophenes for Aromatic Metamorphosis via Diborylbiaryls2017

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

      Chemistry Letters

      Volume: 46 Issue: 8 Pages: 1122-1125

    • DOI

      10.1246/cl.170415

    • NAID

      130005907027

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Regioselective C-H Sulfanylation of Aryl Sulfoxides by Means of Pummerer-Type Activation2017

    • Author(s)
      H. Kawashima, T. Yanagi, C.-C. Wu, K. Nogi, H. Yorimitsu
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 17 Pages: 4552-4555

    • DOI

      10.1021/acs.orglett.7b02147

    • NAID

      120006406843

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Manganese-Catalyzed Ring Opening of Benzofurans and Its Application to Insertion of Heteroatoms into the C2-O Bond2017

    • Author(s)
      Shun Tsuchiya, Hayate Saito, Keisuke Nogi, and Hideki Yorimitsu
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 20 Pages: 5557-5560

    • DOI

      10.1021/acs.orglett.7b02660

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cross-Coupling Reaction of Aryl Sulfoxides with Arylzinc Reagents: When the Leaving Group is an Oxidant2017

    • Author(s)
      Keita Yamamoto, Shinya Otsuka, Keisuke Nogi, and Hideki Yorimitsu
    • Journal Title

      ACS Catal.

      Volume: 7 Issue: 11 Pages: 7623-7628

    • DOI

      10.1021/acscatal.7b02347

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] C-S Bond Alkynylation of Diaryl Sulfoxides with Terminal Alkynes by Means of a Palladium-NHC Catalyst2017

    • Author(s)
      Yuto Yoshida, Keisuke Nogi, and Hideki Yorimitsu
    • Journal Title

      Synlett

      Volume: 28 Issue: 19 Pages: 2561-2564

    • DOI

      10.1055/s-0036-1591676

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Arylation of Benzylic C-H Bonds of Azaarylmethanes with Aryl Sulfides2017

    • Author(s)
      Ke Gao, Keita Yamamoto, Keisuke Nogi, and Hideki Yorimitsu
    • Journal Title

      Synlett

      Volume: 28 Issue: 20 Pages: 2956-2960

    • DOI

      10.1055/s-0036-1589098

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation2017

    • Author(s)
      Kurata, Y.; Otsuka, S.; Fukui, N.; Nogi, K.; Yorimitsu, H.; Osuka, A.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 6 Pages: 1274-1277

    • DOI

      10.1021/acs.orglett.6b03861

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-Catalyzed Boron Insertion into the C2-O Bond of Benzofurans2016

    • Author(s)
      Saito, H.; Otsuka, S.; Nogi, K.; Yorimitsu, H.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 47 Pages: 15315-15318

    • DOI

      10.1021/jacs.6b10255

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] パラジウム触媒を用いたヘテロアリールスルフィドへのイソシアニド挿入2018

    • Author(s)
      大塚慎也 ・野木馨介・依光英樹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research 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2018

    • Author(s)
      齊藤颯 ・野木馨介・依光英樹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] パラジウム触媒による一酸化炭素を用いたアリールスルホニウムのカルボニル化2018

    • Author(s)
      南裕子・野木馨介・依光英樹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] コバルト触媒とアルキルマグネシウム反応剤を用いたアリールスルホンのアレーンへの還元2018

    • Author(s)
      福田淳一 ・野木馨介・依光英樹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research 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
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ニッケル触媒を用いたジアリールスルホンのビアリールへの脱亜硫酸反応2018

    • Author(s)
      高橋郁也 ・野木馨介・依光英樹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ニッケル触媒を用いたアザアレーンとシリルリチウムの反応2018

    • Author(s)
      山岸拓幹・土屋駿・野木馨介・依光英樹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ロジウム触媒によるジベンゾチオフェン類の開環ジボリル化反応2017

    • Author(s)
      齊藤颯, 大塚慎也, 野木馨介, 依光英樹
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ベンゾフラン類の開環反応を利用した2位炭素-酸素間へのヘテロ原子挿入反応2017

    • Author(s)
      土屋駿・齊藤颯・野木馨介 ・依光英樹
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] ロジウム触媒によるジベンゾチオフェン類の開環ジボリル化反応2017

    • Author(s)
      齊藤颯・野木馨介・依光英樹
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] パラジウム触媒によるアリールスルホニウム塩のボリル化2017

    • Author(s)
      南裕子・大塚慎也・野木馨介・依光英樹
    • Organizer
      第6回JACI/GSCシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] ロジウム/銅共触媒によるジベンゾチオフェン類の開環ジボリル化反応2017

    • Author(s)
      齊藤颯・野木馨介・依光英樹
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] マンガン触媒によるベンゾフラン類の開環反応を利用した2位炭素-酸素間へのヘテロ原子挿入2017

    • Author(s)
      土屋駿・齊藤颯・野木馨介・依光英樹
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] パラジウム触媒によるアリールスルホニウム塩のボリル化2017

    • Author(s)
      南裕子・大塚慎也・野木馨介・依光英樹
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] パラジウム触媒によるアリールスルホニウム塩のボリル化2017

    • Author(s)
      南裕子・大塚慎也・野木馨介・依光英樹
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Annual Research Report
  • [Presentation] マンガン触媒によるベンゾフラン類の開環反応を利用した2位炭素-酸素間へのヘテロ原子挿入2017

    • Author(s)
      土屋駿・齊藤颯・野木馨介・依光英樹
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Annual Research Report
  • [Presentation] マンガン触媒によるベンゾフラン類の開環反応を利用した2位炭素-酸素間へのヘテロ原子挿入2017

    • Author(s)
      土屋駿・齊藤颯・野木馨介・依光英樹
    • Organizer
      第7回CSJフェスタ
    • Related Report
      2017 Annual Research 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-硫黄結合へのイソシアニド挿入2017

    • Author(s)
      大塚慎也・野木馨介・依光英樹
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Nickel-Catalyzed Boron Insertion into the C2-O Bond of Benzofurans2017

    • Author(s)
      Hayate Saito・Shinya Otsuka・Keisuke Nogi・Hideki Yorimitsu,
    • Organizer
      Nordic/Kyoto OMCOS 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pd-Catalyzed Borylation of Aryl Sulfonium Salts with Diborons2017

    • Author(s)
      Hiroko Minami・Shinya Otsuka・Keisuke Nogi・Hideki Yorimitsu
    • Organizer
      Nordic/Kyoto OMCOS 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Manganese-Catalyzed Ring-Opening of Benzofurans and its Application to Insertion of Heteroatom into the C2-O Bond2017

    • Author(s)
      Shun Tsuchiya・Hayate Saito・Keisuke Nogi・Hideki Yorimitsu
    • Organizer
      Nordic/Kyoto OMCOS 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pd-Catalyzed Borylation of Aryl Sulfonium Salts with Diborons2017

    • Author(s)
      Hiroko Minami・Shinya Otsuka・Keisuke Nogi・Hideki Yorimitsu
    • Organizer
      19th International Symposium on Organometallic Chemistry Directed towards Organic Synthesis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Palladium-Catalyzed Insertion of Isocyanides into Heteroaryl Sulfides2017

    • Author(s)
      Shinya Otsuka・Keisuke Nogi・Hideki Yorimitsu
    • Organizer
      19th International Symposium on Organometallic Chemistry Directed towards Organic Synthesis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Nickel-Catalyzed Boron Insertion into the C2-O Bond of Benzofurans2017

    • Author(s)
      Hayate Saito・Keisuke Nogi・Hideki Yorimitsu
    • Organizer
      19th International Symposium on Organometallic Chemistry Directed towards Organic Synthesis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Remarks] 研究室ホームページ

    • URL

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

    • Related Report
      2017 Annual Research Report
  • [Remarks] 研究室HP

    • URL

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

    • Related Report
      2016 Annual Research Report

URL: 

Published: 2016-09-02   Modified: 2019-03-29  

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