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Development of Nanospace-Controlled Catalysis towards Challenging Transformation of Saturated Hydrocarbons

Research Project

Project/Area Number 16K13988
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

Iwai Tomohiro  北海道大学, 理学研究院, 助教 (30610729)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords遷移金属錯体触媒 / 配位子設計 / 白金 / 金 / ビスホスフィン / ピンサー配位子 / 遷移金属触媒 / ピンサー型錯体 / 配位子 / ホスフィン / 環化反応 / 飽和炭化水素 / 炭素-水素結合活性化 / ナノ空間触媒 / C-H結合活性化
Outline of Final Research Achievements

The development of nanospace-controlled catalysis towards challenging molecular transformations, focusing on direct functionalization of saturated hydrocarbons, was carried out. Cationic gold(I) complexes with hollow-shaped triethynylphosphine ligands efficiently catalyzed intramolecular [2+2] cycloaddition of 1,9-enynes to afford cyclobutene-fused eight-membered carbocycles. For construction of precise catalytic environments, bulky P-alkynyl-substituted bisphosphine and PCP-pincer-type ligands were designed and synthesized. These polydentate ligands were applied to Pt(II)-catalyzed cycloisomerization of 1,8-enynes.

Report

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

    (38 results)

All 2018 2017 2016 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (27 results) (of which Int'l Joint Research: 3 results,  Invited: 6 results) Remarks (2 results)

  • [Journal Article] Phosphine-Catalyzed anti-Carboboration of Alkynoates with 9-BBN-Based 1,1-Diborylalkanes: Synthesis and Use of Multisubstituted γ-Borylallylboranes2018

    • Author(s)
      Yamazaki Ayaka、Nagao Kazunori、Iwai Tomohiro、Ohmiya Hirohisa、Sawamura Masaya
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 12 Pages: 3196-3199

    • DOI

      10.1002/anie.201712351

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed amination of aryl fluorides with primary amines2018

    • Author(s)
      Harada Tomoya、Ueda Yusuke、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 14 Pages: 1718-1721

    • DOI

      10.1039/c7cc08181b

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Cyclobutene-Fused Eight-Membered Carbocycles through Gold-Catalyzed Intramolecular Enyne [2+2] Cycloaddition2017

    • Author(s)
      Iwai Tomohiro、Ueno Masahiro、Okochi Hiori、Sawamura Masaya
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 360 Issue: 4 Pages: 670-675

    • DOI

      10.1002/adsc.201701193

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Rh- or Ir-catalyzed Directed C(sp<sup>3</sup>)–H Borylation with Phosphoramidite Chiral Ligands2017

    • Author(s)
      Reyes Ronald L.、Harada Tomoya、Taniguchi Tohru、Monde Kenji、Iwai Tomohiro、Sawamura Masaya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 12 Pages: 1747-1750

    • DOI

      10.1246/cl.170853

    • NAID

      130006243163

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Polystyrene-Cross-Linking Ortho-Substituted Triphenylphosphines: Synthesis, Coordination Properties, and Application to Pd-Catalyzed Cross-Coupling of Aryl Chlorides2017

    • Author(s)
      Tomohiro Iwai, Kiichi Asano, Tomoya Harada, Masaya Sawamura
    • Journal Title

      Bulletine of Chemical Society of Japan

      Volume: 90 Issue: 8 Pages: 943-949

    • DOI

      10.1246/bcsj.20170141

    • NAID

      130005973622

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of β‐Lactams through Copper‐Catalyzed Alkyne‐Nitrone Coupling with Prolinol‐Phosphine Chiral Ligand2017

    • Author(s)
      Yurie Takayama, Takaoki Ishii, Hirohisa Ohmiya, Tomohiro Iwai, Martin C. Schwarzer, Seiji Mori, Tohru Taniguchi, Kenji Monde, Masaya Sawamura
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Issue: 35 Pages: 8400-8404

    • DOI

      10.1002/chem.201702070

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Polystyrene-Cross-Linking Bisphosphine: Controlled Metal Monochelation and Ligand-Enabled First-Row Transition Metal Catalysis2017

    • Author(s)
      Tomohiro Iwai, Tomoya Harada, Hajime Shimada, Kiichi Asano, Masaya Sawamura
    • Journal Title

      ACS Catalysis

      Volume: 7 Issue: 3 Pages: 1681-1692

    • DOI

      10.1021/acscatal.6b02988

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Coordination Properties, and Catalytic Application of Triarylmethane-Monophosphines2016

    • Author(s)
      Tomohiro Iwai, Ryotaro Tanaka, Masaya Sawamura
    • Journal Title

      Organometallics

      Volume: 35 Issue: 23 Pages: 3959-3969

    • DOI

      10.1021/acs.organomet.6b00752

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] ベースメタルの可能性を引きだす2016

    • Author(s)
      岩井 智弘
    • Journal Title

      化学

      Volume: 71 Pages: 59-60

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] Multipoint Solid-Supported Phosphine Ligands for Efficient Organometallic Catalysis2018

    • Author(s)
      Tomohiro Iwai
    • Organizer
      日本化学会 第98春季年会 (2018) アジア国際シンポジウム
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 芳香族カルバメートの脱炭酸アミノ化反応の開発とその機構研究2018

    • Author(s)
      鳶巣守・西澤彰宏・岩井智弘・澤村正也・茶谷直人
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Rhodium- or Iridium-Catalyzed Enantioselective C(sp3)-H Borylation with Chiral Monophosphine Ligands2018

    • Author(s)
      Ronald Reyes, Tomoya Harada, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] ポリスチレン架橋トリアルキルホスフィンの合成とパラジウム触媒クロスカップリングへの応用2018

    • Author(s)
      荒島純弥・岩井智弘・澤村正也
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Transfer Hydrogenation of Alkenes Using 1,4-Dioxane as a Hydrogen Source Catalyzed by a Polystyrene-Cross-Linking Bisphosphine-Iridium Complex2018

    • Author(s)
      Deliang Zhang, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] ポリスチレン架橋ビスホスフィン-ニッケル触媒による有機リチウム化合物のクロスカップリング2018

    • Author(s)
      有馬望・岩井智弘・澤村正也
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ni-catalyzed Murahashi Coupling in Polystyrene Gel2018

    • Author(s)
      Nozomi Arima,Tomohiro Iwai, Masaya Sawamura
    • Organizer
      IRCCS-JST CREST Joint Symposium “Chemical Sciences facing difficult challenges"
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 反応場の特性を活かした高活性金属錯体触媒の設計2018

    • Author(s)
      岩井智弘
    • Organizer
      平成29年度 日本化学会北海道支部奨励賞 受賞講演
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] トリアリールメタン-モノホスフィン:合成、配位特性およびPd触媒共役付加反応への適用2017

    • Author(s)
      岩井 智弘・田中 遼太郎・澤村 正也
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] A Phosphine Cross-Linked Method for Producing Highly Active Heterogeneous Transition Metal Catalysts2017

    • Author(s)
      Tomohiro Iwai・Tomoya Harada・Hajime Shimada・Kiichi Asano・Deliang Zhang・Shigenori Chiba・Masaya Sawamura
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] ニッケル触媒によるフッ化アリールと第一級アミンのクロスカップリング反応2017

    • Author(s)
      原田 友哉・岩井 智弘・澤村 正也
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Palladium-Catalyzed Enantioselective Side Chain C(α) Allylation of 2-Alkylazaarenes2017

    • Author(s)
      Ryo Murakami・Tomohiro Iwai・Masaya Sawamura
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] ボレート含有かご型トリアリールホスフィンの合成と配位特性2017

    • Author(s)
      小西 菖太・岩井 智弘・澤村 正也
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 固相担体の特性を活かした高活性金属錯体触媒の創製2017

    • Author(s)
      岩井智弘
    • Organizer
      2017年度 触媒学会北海道支部 札幌講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 固相多点担持法による高活性金属錯体触媒の設計開発2017

    • Author(s)
      岩井智弘
    • Organizer
      第1回産総研化学研究シンポジウム「夢見る30代化学者たちの挑戦」
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Catalytic Asymmetric Heteroatom-Directed C(sp3)-H Borylation with Chiral Monophosphine Ligands2017

    • Author(s)
      Ronald L. Reyes, Tomoya Harada, Tomohiro Iwai, Masaya Sawamura
    • Organizer
      The 12th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Related Report
      2017 Annual Research Report
  • [Presentation] 銅触媒不斉アルキンーニトロンカップリングによるβ-ラクタムの不斉合成2017

    • Author(s)
      今井洸児・高山ゆりえ・石井孝興・大宮寛久・岩井智弘・Schwarzer Martin・佐藤丈弘・森聖治・澤村正也
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Theoretical Studies on Pd-Catalyzed Enantioselective Direct Allylation of 2-Alkylpyridines at the Side Chain α-Position2017

    • Author(s)
      Kyohei Kawashima, Ryo Murakami, Kentaro Sano, Tomohiro Iwai, Masaya Sawamura, Seiji Mori
    • Organizer
      錯体化学会 第67回討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 第一級アミンによるフッ化アリールのニッケル触媒アミノ化反応2017

    • Author(s)
      岩井智弘、原田友哉、澤村正也
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] キラルモノホスフィン配位子を用いた触媒的不斉 C(sp3)-H ホウ素化反応2017

    • Author(s)
      Ronald L. Reyes ・原田友哉・岩井智弘・澤村正也
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 塩基フリーパラジウム触媒による 2-アルキルピリジンの不斉 C(sp3)-H アリル化反応2017

    • Author(s)
      村上遼 ・佐野建太郎・岩井智弘・澤村正也
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Catalytic Enantioselective C(sp3)-H Borylation Reactions using Chiral Monophosphine Ligands2017

    • Author(s)
      Ronald L. Reyes, Tomoya Harada, Tomohiro Iwai, and Masaya Sawamura
    • Organizer
      第29回 万有札幌シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Polystyrene-Cross-Linking Phosphine Ligands for Producing Highly Active Metal Catalysts2017

    • Author(s)
      Tomohiro Iwai
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC) 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] かご型ボレートホスフィンの合成と性質2017

    • Author(s)
      小西菖太・岩井智弘・澤村正也
    • Organizer
      第111回有機合成シンポジウム2017年【春】
    • Related Report
      2017 Annual Research Report
  • [Presentation] 固相多点担持ホスフィンによる次世代型不均一系遷移金属触媒の開発2016

    • Author(s)
      岩井 智弘
    • Organizer
      分子研若手研究会「若い世代が創る次世代型分子触媒の開発とその展望」
    • Place of Presentation
      分子科学研究所(愛知県・岡崎市)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Creation of Highly Active First-Row Transition Metal Catalysts Based on Coordination Abilities of a Polystyrene-Cross-Linking Bisphosphine2016

    • Author(s)
      Tomohiro Iwai・Tomoya Harada・Hajime Shimada・Kiichi Asano・Masaya Sawamura
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学(東京都・新宿区)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] ポリスチレン架橋ビスホスフィン:第一周期遷移金属触媒における顕著なポリマー効果2016

    • Author(s)
      原田 友哉・岩井 智弘・島田 肇・浅野 輝一・澤村 正也
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      ヒルトンニセコビレッジ(北海道・ニセコ町)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Research-status Report
  • [Remarks] 北海道大学大学院理学研究院化学部門 有機金属化学研究室

    • URL

      http://wwwchem.sci.hokudai.ac.jp/~orgmet/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 北海道大学大学院理学研究院化学部門 有機金属化学研究室

    • URL

      http://wwwchem.sci.hokudai.ac.jp/~orgmet/

    • Related Report
      2016 Research-status Report

URL: 

Published: 2016-04-21   Modified: 2019-03-29  

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