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Synthesis of boron-containing organic materials by novel nucleophilic borylation

Research Project

Project/Area Number 15H03804
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

Ito Hajime  北海道大学, 工学研究院, 教授 (90282300)

Co-Investigator(Kenkyū-buntansha) 石山 竜生  北海道大学, 工学研究院, 准教授 (00232348)
関 朋宏  北海道大学, 工学研究院, 助教 (50638187)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥17,160,000 (Direct Cost: ¥13,200,000、Indirect Cost: ¥3,960,000)
Fiscal Year 2017: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2015: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Keywords銅(I)触媒 / 塩基触媒 / 有機ホウ素化合物 / 不斉合成 / ホウ素化 / 環化ホウ素化 / ラジカル反応 / 脱芳香族化 / ホウ素 / 有機合成 / 脱芳香族化反応 / DFT計算 / 合成化学 / 有機工業化学 / 有機化学
Outline of Final Research Achievements

In this research, by using copper-catalyzed reactions and base-mediated reactions, we developed many useful synthetic reactions of organoboron compounds: alkyl-, alkenyl-, aryl, alkynyl halides, ketones, aldehydes, indole, pyridine, quinoline derivatives were applied to the boryl substitution reaction, boryl addition reaction, boryl cyclization reactions, dearomative borylations. We also develop asymmetric catalytic borylation through applying chiral catalysts to some of these new reactions. This research project afforded a significant amount of results of the development of many synthetic reactions of organoboron compounds, which are useful reagents on organic synthesis.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (48 results)

All 2018 2017 2016 2015 Other

All Int'l Joint Research (3 results) Journal Article (19 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 19 results,  Open Access: 2 results,  Acknowledgement Compliant: 10 results) Presentation (23 results) (of which Int'l Joint Research: 8 results,  Invited: 10 results) Remarks (2 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] スイス連邦工科大学・チューリッヒ校(スイス)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] スイス連邦工科大学(スイス)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] スイス連邦工科大学チューリッヒ校(スイス)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Copper(I)-Catalyzed Stereo- and Chemoselective Borylative Radical Cyclization of Alkyl Halides Bearing an Alkene Moiety2017

    • Author(s)
      Iwamoto Hiroaki、Akiyama Sota、Hayama Keiichi、Ito Hajime
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 10 Pages: 2614-2617

    • DOI

      10.1021/acs.orglett.7b00940

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal Nucleophilic Silyl Substitution of Aryl Halides with Silyllithium Reagents via Halogenophilic Attack of Silyl Nucleophiles2017

    • Author(s)
      Ito Hajime、Yamamoto Eiji、Ukigai Satoshi
    • Journal Title

      Synlett

      Volume: 28 Issue: 18 Pages: 2460-2464

    • DOI

      10.1055/s-0036-1590835

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Tris(trimethylsilyl)silylboronate Esters: Novel Bulky, Air- and Moisture-Stable Silylboronate Ester Reagents for Boryl Substitution and Silaboration Reactions2017

    • Author(s)
      Yamamoto Eiji、Shishido Ryosuke、Seki Tomohiro、Ito Hajime
    • Journal Title

      Organometallics

      Volume: 36 Issue: 16 Pages: 3019-3022

    • DOI

      10.1021/acs.organomet.7b00476

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereodivergent hydrodefluorination of gem-difluoroalkenes: selective synthesis of (Z)- and (E)-monofluoroalkenes2017

    • Author(s)
      Kojima Ryoto、Kubota Koji、Ito Hajime
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 77 Pages: 10688-10691

    • DOI

      10.1039/c7cc05225a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate2017

    • Author(s)
      Taguchi Jumpei、Ikeda Toshiki、Takahashi Rina、Sasaki Ikuo、Ogasawara Yasushi、Dairi Tohru、Kato Naoya、Yamamoto Yasunori、Bode Jeffrey W.、Ito Hajime
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 44 Pages: 13847-13851

    • DOI

      10.1002/anie.201707933

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Copper(I)-Catalyzed Regio- and Stereoselective Intramolecular Alkylboration of Propargyl Ethers and Amines2017

    • Author(s)
      Iwamoto Hiroaki、Ozawa Yu、Kubota Koji、Ito Hajime
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 19 Pages: 10563-10573

    • DOI

      10.1021/acs.joc.7b02071

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(I)-catalyzed Diastereoselective Dearomative Carboborylation of Indoles2017

    • Author(s)
      Hayama Keiichi、Kubota Koji、Iwamoto Hiroaki、Ito Hajime
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 12 Pages: 1800-1802

    • DOI

      10.1246/cl.170825

    • NAID

      130006243185

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Ketones: Synthesis of Enantioenriched Chiral Tertiary alpha-Hydroxyboronates2017

    • Author(s)
      Kubota, K.; Osaki, S.; Jin, M.; Ito, H.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 印刷中

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper(I)-Catalyzed Boryl Substitution of Allyl Aminals: Selective Synthesis of Linear γ-Aminoallylboronates2017

    • Author(s)
      Takenouchi, Y.; Ito, H.
    • Journal Title

      Synthesis

      Volume: 印刷中

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Transition-Metal-Free Boryl Substitution using Silylboranes and Alkoxy Bases2017

    • Author(s)
      Yamamoto, E.; Maeda, S.; Taketsugu, T.; Ito, H.
    • Journal Title

      Synlett

      Volume: 印刷中

    • NAID

      120006484242

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper(I)-Catalyzed Enantioselective Boryl Substitution of Allyl Acylals: An Efficient Approach for Enantioenriched α-Chiral γ-Acetoxyallylboronates2017

    • Author(s)
      Takenouchi, Y.; Kojima, R.; Momma, R.; Ito, H.
    • Journal Title

      Synlett

      Volume: 28 Issue: 02 Pages: 270-274

    • DOI

      10.1055/s-0036-1588354

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane2016

    • Author(s)
      Yamamoto, E; Izumi, K.; Shishido, R.; Seki, T.; Tokodai, N.; Ito, H.
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 49 Pages: 17547-17551

    • DOI

      10.1002/chem.201604021

    • NAID

      120006366477

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Enantiomerically Enriched Chiral Tetrahydroquinolines via Sequential Dearomatization/Enantioselective Borylation Reactions2016

    • Author(s)
      Kubota, K.; Watanabe, Y.; Ito, H.
    • Journal Title

      Adv. Synth. Catal.

      Volume: 15 Issue: 15 Pages: 2379-2384

    • DOI

      10.1002/adsc.201600372

    • NAID

      120006331853

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Computational Insight into the Enantioselective Nucleophilic Borylation of a Polarized C=O Double Bond Catalyzed by Di-phosphine-Borylcopper(I) Complexes2016

    • Author(s)
      Kubota, K.; Jin, M.; Ito, H.
    • Journal Title

      Organometallics

      Volume: 35 Issue: 10 Pages: 1376-1383

    • DOI

      10.1021/acs.organomet.5b00621

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Selective Markovnikov Hydroboration of Alkyl-Substituted Terminal Alkenes with a Phosphine-Copper(I) Catalyst2016

    • Author(s)
      Iwamoto, H.; Kubota, K.; Ito, H.
    • Journal Title

      Chem. Commun.

      Volume: 印刷中 Issue: 35 Pages: 5916-5919

    • DOI

      10.1039/c6cc00782a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines2016

    • Author(s)
      Kubota, K.; Watanabe, Y.; Hayama, K.; Ito, H.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 13 Issue: 13 Pages: 4338-4341

    • DOI

      10.1021/jacs.6b01375

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Boryl substitution of functionalized aryl-, heteroaryl-, and alkenyl halides with silylborane and alkoxy base: expanded scope and mechanistic studies2015

    • Author(s)
      Eiji Yamamoto, Satoshi Ukigai, Hajime Ito
    • Journal Title

      Chemical Science

      Volume: 6 Issue: 5 Pages: 2943-2951

    • DOI

      10.1039/c5sc00384a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Enantioselective Borylative Dearomatization of Indoles through Copper(I) Catalysis2015

    • Author(s)
      Kubota, K.; Hayama, K.; Iwamoto, H.; Ito, H.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 54 Issue: 30 Pages: 8809-8813

    • DOI

      10.1002/anie.201502964

    • NAID

      120005763139

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(I)-Catalyzed Diastereoselective Borylative Exo-Cyclization of Alkenyl Aryl Ketones2015

    • Author(s)
      Copper(I)-Catalyzed Diastereoselective Borylative Exo-Cyclization of Alkenyl Aryl Ketones
    • Journal Title

      Synlett

      Volume: 26 Issue: 02 Pages: 272-276

    • DOI

      10.1055/s-0035-1560721

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] シリル基を有するアリルホウ素化合物を用いた銅(I)触媒による立体選択的アリル化反応2018

    • Author(s)
      林 優太・岩本 紘明・伊藤 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 銅(I)触媒によるアレンの分子内アルキルホウ素化反応2018

    • Author(s)
      小澤 友・岩本 紘明・伊藤 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of Chiral Bisphosphine Ligand Design Method for Copper(I)-catalyzed Enantioselective Markovnikov Hydroboration of Aliphatic Terminal Alkenes2018

    • Author(s)
      IWAMOTO, Hiroaki; IMAMOTO, Tsuneo; ITO, Hajime
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ペプチドへのアシルボロン構造導入ユニットとなるα-アミノアシルボロンの合成2018

    • Author(s)
      高橋 里奈・田口 純平・Bode Jeffrey W.・伊藤 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Cu(I) 触媒によるアルデヒドのホウ素化と続く酸化によるアシルホウ素化合物の合成2018

    • Author(s)
      竹内 拓未・田口 純平・伊藤 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Copper(I)-Catalyzed Stereodivergent Hydrodefluorination of gem-Difluoroalkenes2018

    • Author(s)
      KOJIMA, Ryoto; KUBOTA, Koji; ITO, Hajime
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 銅(I)触媒による脂肪族gem-ジフルオロアルケンに対する立体選択的脱フッ素ホウ素化反応2018

    • Author(s)
      瀬尾 珠恵・小島 遼人・伊藤 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 銅(I)触媒によるβ-フッ素脱離を伴う新規不斉ホウ素化反応の開発2018

    • Author(s)
      秋山 颯太・小島 遼人・伊藤 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 銅(I)触媒による脂肪族ケトン及びケチミンに対する不斉ホウ素化反応2018

    • Author(s)
      大崎 駿・久保田 浩司・伊藤 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Iridium-Catalyzed C-H Dimesitylborylation of Benzofurans with Silyldimesitylborane2018

    • Author(s)
      SHISHIDO, Ryosuke; SASAKI, Ikuo; SEKI, Tomohiro; ISHIYAMA, Tatsuo; ITO, Hajime
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ligand-Controlled Chemoselectivity of Copper(I)-Catalyzed Borylation Reaction and Development of Borylative Radical Cyclization2017

    • Author(s)
      IWAMOTO, Hiroaki; KUBOTA, Koji; AKIYAMA, Sota; ITO, Hajime
    • Organizer
      日本化学会第97回春季年会
    • Place of Presentation
      慶応義塾大学理工学部, 東京
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Copper-Catalyzed Borylation with Diboron: The Beginning and Our Recent Results2017

    • Author(s)
      Hajime Ito
    • Organizer
      BK21+/Basic Science Research Institute (POSTECH) Mini-Symposium, Frontiers in Organic and Organometallic Chemistry
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper-Catalyzed Asymmetric Borylative Dearomatization: New Pathway to Optically Active Heterocyclic Compounds2017

    • Author(s)
      Hajime Ito
    • Organizer
      16th International Meeting on Boron Chemistry
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ソフトクリスタルの結晶相転移をデザインする方法2017

    • Author(s)
      伊藤肇
    • Organizer
      新学術領域研究 ソフトクリスタル 第1回公開シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Anomalous reactivity of silylborane: Boryl substitution of organic halides with silylborane/alkoxy base systems2016

    • Author(s)
      Hajime Ito
    • Organizer
      Pacifichem2015
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2016-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper-Catalyzed Borylation: the Discovery and the Recent Progress2016

    • Author(s)
      Hajime Ito
    • Organizer
      第26回光学活性化合物シンポジウム
    • Place of Presentation
      日本薬学会館長井記念ホール, 東京
    • Year and Date
      2016-11-25
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 銅(I)触媒による光学活性有機ホウ素化合物の新しい合成法2016

    • Author(s)
      伊藤肇
    • Organizer
      京都大学集中講義、特別講演会
    • Place of Presentation
      京都大学、京都市
    • Year and Date
      2016-11-22
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Copper-catalyzed borylations: from the beginning to our recent study2016

    • Author(s)
      Hajime Ito
    • Organizer
      湖北工業大学講演会
    • Place of Presentation
      湖北工業大学, 武漢市, 中国
    • Year and Date
      2016-04-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper-catalyzed borylations: from the beginning to our recent study2016

    • Author(s)
      Hajime Ito
    • Organizer
      中国科学院成都生物研究所講演会
    • Place of Presentation
      中国科学院成都生物研究所, 成都市, 中国
    • Year and Date
      2016-04-25
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 銅(I)触媒による1,2-ジヒドロピリジンの位置およびエナンチオ選択的ホウ素化反応2016

    • Author(s)
      久保田 浩司・渡邉 裕太・羽山 慶一・伊藤 肇
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Enantioselective Borylative Dearomatization of Indoles Using Copper2015

    • Author(s)
      Keiichi Hayama, Koji Kubota, Hiroaki Iwamoto, Hajime Ito
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学(吹田市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] Strange reactivity of silylborane: Boryl substitution of organic halides with silylborane/alkoxy base systems2015

    • Author(s)
      Hajime Ito
    • Organizer
      IUPAC Symposium
    • Place of Presentation
      Busan, Korea
    • Year and Date
      2015-08-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Copper-Catalyzed and Base-Promoted Borylations2015

    • Author(s)
      Hajime Ito
    • Organizer
      Stockholm University 講演会
    • Place of Presentation
      Stockholm, Sweden
    • Year and Date
      2015-06-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Remarks] 有機元素化学研究室

    • URL

      http://labs.eng.hokudai.ac.jp/labo/organoelement/

    • Related Report
      2017 Annual Research Report
  • [Remarks]

    • URL

      http://labs.eng.hokudai.ac.jp/labo/organoelement/

    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] アミノ酸型アシルボランおよびその製造方法2017

    • Inventor(s)
      伊藤肇、田口純平、池田俊希
    • Industrial Property Rights Holder
      伊藤肇、田口純平、池田俊希
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017-02-28
    • Related Report
      2016 Annual Research Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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