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Development of addition reaction of an E-H bond (E = main group elements having lone pair electrons) to alkynes catalyzed by an iron complex

Research Project

Project/Area Number 25410073
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Inorganic chemistry
Research InstitutionOsaka City University

Principal Investigator

ITAZAKI Masumi  大阪市立大学, 大学院理学研究科, 講師 (60382032)

Co-Investigator(Kenkyū-buntansha) 中沢 浩  大阪市立大学, 大学院理学研究科, 教授 (00172297)
Project Period (FY) 2013-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords鉄触媒 / ヒドロホスフィン化 / アルキン / インジウム / ヒドロシリル化 / ニトリル / アセチレン / 鉄 / ビニルホスフィン / 2級ホスフィン / 非対称ジホスフィン
Outline of Final Research Achievements

Iron complex-catalyzed regioselective single hydrophosphination of terminal arylalkyne with secondary phosphine was achieved. Unsymmetric 1,2-bis(phosphino)ethanes with different phosphino groups were obtained by using our catalytic systems. The structures of obtained vinylphosphine, unsymmetric 1,2-bis(phosphino)ethane, and iron catalyst precursors were confirmed by single crystal X-ray diffraction studies. In addition, Selective double hydrosilylation was achieved by using tertiary and secondary silanes with an excess amount of an organonitrile (RC≡N; R = alkyl, aryl) in the presence of a catalytic amount of triirondodecacarbonyl [Fe3(CO)12] and indium trichloride (InCl3). This reaction was also catalyzed by an iron complex containing indium trihalide [Fe(MeCN)6][Fe(CO)4(InCl3)2], prepared by the reaction of Fe3(CO)12 with InCl3. This is a novel report of the combination of a transition-metal complex and an indium source in organic synthesis.

Report

(5 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (45 results)

All 2017 2016 2015 2014 2013

All Journal Article (10 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 10 results,  Acknowledgement Compliant: 6 results) Presentation (34 results) (of which Int'l Joint Research: 4 results,  Invited: 4 results) Book (1 results)

  • [Journal Article] R/X exchange reactions in cis-[M(R)2{P(X)(NMeCH2)2}2] (M = Pd, Pt), via a phosphenium intermediate2016

    • Author(s)
      M. Itazaki, N. Tsuchida, Y. Shigesato, K. Takano, H. Nakazawa
    • Journal Title

      Dalton Trans.

      Volume: 45 Issue: 48 Pages: 19216-19220

    • DOI

      10.1039/c6dt02314b

    • NAID

      120006376423

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019796

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hydrogenation of Chlorosilanes by NaBH_42016

    • Author(s)
      M. Ito, M. Itazaki, T. Abe. H. Nakazawa
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 12 Pages: 1434-1436

    • DOI

      10.1246/cl.160808

    • NAID

      130005475731

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019741

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective Double Hydrosilylation of Nitriles Catalyzed by an Iron Complex Containing Indium Trihalide2016

    • Author(s)
      M. Ito, M. Itazaki, H. Nakazawa
    • Journal Title

      ChemCatChem

      Volume: 8 Issue: 21 Pages: 3323-3325

    • DOI

      10.1002/cctc.201600940

    • NAID

      120006532430

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019708

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Tetrahedral cage complex with planar vertices : selective synthesis of Pt_4L_6 cage complexes involving hydrogen bonds driven by halide binding2016

    • Author(s)
      M. Ito, M. Iseki, M. Itazaki, H. Nakazawa
    • Journal Title

      Chem. Commun.

      Volume: 52 Issue: 45 Pages: 7205-7208

    • DOI

      10.1039/c6cc01448h

    • NAID

      120006576128

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019714

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and characterization of [Fe(NCCH_3)_6][cis-Fe(InX_3)_2(CO)_4](X=Cl, Br, I) containing two terminal indium fragments2016

    • Author(s)
      Masumi Itazaki, Masaki Ito, Hiroshi Nakazawa
    • Journal Title

      Dalton Trans.

      Volume: 45 Issue: 4 Pages: 1327-1330

    • DOI

      10.1039/c5dt03745j

    • NAID

      120006576130

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019795

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of vinylphosphines and unsymmetric diphosphines : iron-catalyzed selective hydrophosphination reaction of alkynes and vinylphosphines with secondary phosphines2016

    • Author(s)
      Masumi Itazaki, Shinya Katsube, Masahiro Kamitani, Hiroshi Nakazawa
    • Journal Title

      Chem. Commun.

      Volume: 52 Issue: 15 Pages: 3163-3166

    • DOI

      10.1039/c5cc10185a

    • NAID

      120006576129

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019713

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Electronic Lability in a Dinuclear Cobalt Bis-dioxolene Complex2015

    • Author(s)
      Azadeh Madadi, Masumi Itazaki, Robert W. Gable, Boujemaa Moubaraki, Keith S. Murray, Colette Boskovic
    • Journal Title

      Eur. J. Inorg. Chem.

      Volume: 0 Issue: 30 Pages: 4991-4995

    • DOI

      10.1002/ejic.201500980

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Effective Dehydrogenation of 2-Pyridylmethanol Derivatives Catalyzed by an Iron Complex2014

    • Author(s)
      神谷昌宏、夛田亮介、板崎真澄、中沢浩
    • Journal Title

      Chemical Communication

      Volume: 50(In press) Issue: 59 Pages: 7941-7944

    • DOI

      10.1039/c4cc01498g

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Fe-H/Si-H and Fe-H/Ge-H Bifunctional Complexes and Their Catalytic Hydrogenation Reaction toward Non-polar Unsaturated Organic Molecules2014

    • Author(s)
      神谷昌宏、西口佳範、多田、板崎真澄、中沢浩
    • Journal Title

      Organometallics

      Volume: 33 Issue: 7 Pages: 1532-1535

    • DOI

      10.1021/om5000562

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective Boryl Silyl Ether Formation in the Photoreaction of Bisboryloxide/Boroxine with Hydrosilane Catalyzed by a Transition-Metal Carbonyl Complex2014

    • Author(s)
      M. Ito, M. Itazaki, H. Nakazawa
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 17 Pages: 6183-6186

    • DOI

      10.1021/ja500465x

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] 鉄の特長を活かした有機合成反応の開発-典型元素-水素結合の炭素-炭素不飽和結合への選択的な付加-2017

    • Author(s)
      板崎真澄
    • Organizer
      ヘテロ原子部会平成 28 年度第 3 回懇話会
    • Place of Presentation
      大阪科学技術センター 大阪府大阪市
    • Year and Date
      2017-02-06
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 低毒性な鉄を触媒とするリン化合物の新規合成法の創製2016

    • Author(s)
      板崎真澄
    • Organizer
      大阪府立大学・大阪市立大学ニューテクフェア2016
    • Place of Presentation
      大阪産業創造館 大阪府大阪市
    • Year and Date
      2016-12-06
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 鉄メチル錯体を触媒前駆体とする様々な有機合成反応と、その中間体錯体の反応性2016

    • Author(s)
      板崎真澄
    • Organizer
      第55回錯体化学若手の会近畿地区勉強会
    • Place of Presentation
      奈良女子大学 奈良県奈良市
    • Year and Date
      2016-11-19
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] ハロゲン化インジウムを有する鉄錯体を触媒として用いた選択的ダブルヒドロシリル化、ダブルヒドロボリル化およびジヒドロシリルボリル化反応の開発2016

    • Author(s)
      伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀 東京都江戸川区
    • Year and Date
      2016-11-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] 鉄錯体触媒を用いたC≡C 三重結合への段階的なP-H結合付加反応2016

    • Author(s)
      板崎真澄、勝部伸哉、後田朋哉、中沢 浩
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学 西早稲田キャンパス 東京都新宿区
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] Syntheses of Cage-Ahaped Complexes with Platinum or Palladium Planar Vertices and Their Structures -Reactions of Dihalogeno Platium or Palladium Complexes with Phosphinecarboxyakide-2016

    • Author(s)
      Masaki Ito, Masato Iseki, Masumi Itazaki, Takuya Otani, Hiroshi Nakazawa
    • Organizer
      錯体化学会第66回討論会
    • Place of Presentation
      福岡大学 七隈キャンパス 福岡県福岡市
    • Year and Date
      2016-09-10
    • Related Report
      2016 Annual Research Report
  • [Presentation] ハロゲン化インジウムを配位子とするルテニウム錯体の反応性2016

    • Author(s)
      板崎真澄、土橋由夏子、伊藤昌輝、中沢 浩
    • Organizer
      錯体化学会第66回討論会
    • Place of Presentation
      福岡大学 七隈キャンパス 福岡県福岡市
    • Year and Date
      2016-09-10
    • Related Report
      2016 Annual Research Report
  • [Presentation] Regioselective Hydrophosphination Reaction of a C≡C Triple Bond Catalyzed by an Iron Complex and Isolation of Intermediate Complexes2016

    • Author(s)
      Masumi Itazaki
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC) 2016
    • Place of Presentation
      Kuching, Sarawak, Malaysia
    • Year and Date
      2016-08-15
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 平面四配位白金錯体を頂点構造とする白金四核かご状錯体 Pt4L6 の選択的合成2016

    • Author(s)
      伊藤昌輝、井関柾登、板崎真澄、中沢 浩
    • Organizer
      第14回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      高知城ホール 高知県高知市
    • Year and Date
      2016-06-04
    • Related Report
      2016 Annual Research Report
  • [Presentation] 鉄錯体を触媒とする末端アルキンの位置選択的なヒドロチオ化反応とその立体選択性の考察2016

    • Author(s)
      後田朋哉、板崎真澄、勝部伸哉、中村 渉、中沢 浩
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      ANAクラウンプラザホテル神戸 兵庫県神戸市
    • Year and Date
      2016-06-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] 鉄錯体を触媒とする末端アルキンの段階的なヒドロホスフィン化を用いた非対称1,2-ビスホスフィノエタンの合成2016

    • Author(s)
      板崎真澄、勝部伸哉、神谷昌宏、中沢 浩
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      ANAクラウンプラザホテル神戸 兵庫県神戸市
    • Year and Date
      2016-06-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] 鉄錯体触媒を用いたアリールアルキンの位置選択的なヒドロチオ化反応2016

    • Author(s)
      板崎 真澄、後田朋哉、勝部伸哉、中村 渉、中沢 浩
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都都、京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Formation of Indium-iron Complexes and the Catalytic Activity toward Double Hydrosilylation of Nitriles2015

    • Author(s)
      M. Ito, M. Itazaki, S. Nakashima, H. Nakazawa
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] R/X Exchange Reaction on Pd and Pt Complexes with Phosphine Ligand, cis-[MR2{P(MeNCH2)2X}2] (M = Pd, Pt) via an Intermediate of Phosphenium Complex2015

    • Author(s)
      M. Itazaki, Y. Shigesato, N Tsuchida, K. Takano, H. Nakazawa
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Regioselective P-H Bond Addition to a Multiple C-C Bond Catalyzed by an Iron Complex2015

    • Author(s)
      S. Katsube, M. Itazaki, H. Nakazawa
    • Organizer
      The 19th Osaka City University International Workshop on Advanced Molecular Materials Science
    • Place of Presentation
      大阪市立大学(大阪府、大阪市)
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] インジウム配位子を有する鉄錯体を用いたニトリル化合物の触媒的ダブルヒドロシリル化反応の開発2015

    • Author(s)
      伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京都、江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 1,1’-ビス(フェニルホスフィノ)フェロセンと0価白金ホスフィン錯体の反応―生成錯体の構造とホスフィン配位子の関係―2015

    • Author(s)
      板崎真澄、市山友紀、久保田陽子、中沢 浩
    • Organizer
      錯体化学会第65回討論会
    • Place of Presentation
      奈良女子大学(奈良県、奈良市)
    • Year and Date
      2015-09-21
    • Related Report
      2015 Research-status Report
  • [Presentation] インジウム-鉄混合金属錯体を配位子として用いたニトリルの選択的ダブルヒドロシリル化反応によるジシリルアミン合成反応2015

    • Author(s)
      伊藤昌輝、板崎真澄、中島 覚、中沢 浩
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県、福岡市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] ホスフィンカルボキシアミド (RNHC(O)PR’2) とハロゲン間の水素結合形成を鍵とするかご状白金錯体の合成2014

    • Author(s)
      井関柾登、伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部市文化会館文化ホール(宇部市、山口県)
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 新規機能性無機材料開発を志向した遷移金属錯体触媒による選択的ホウ素-ケイ素結合形成反応の創製2014

    • Author(s)
      伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      第4回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(江戸川区、東京都)
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] Achievement of Boron-Oxygen-Silicon Alignment Promoted by a Transition Metal Catalysis: Selective Synthesis of Boryl Silyl Ethers2014

    • Author(s)
      伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学、病院キャンパス(福岡市、福岡県)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] 鉄触媒を用いたヒドロホスフィン化によるビニルホスフィンの合成および中間体錯体の単離2014

    • Author(s)
      勝部伸哉、板崎真澄、神谷昌宏、中沢 浩
    • Organizer
      錯体化学会第64回討論会
    • Place of Presentation
      中央大学、後楽園キャンパス(文京区、東京都)
    • Year and Date
      2014-09-18 – 2014-09-20
    • Related Report
      2014 Research-status Report
  • [Presentation] Selective Hydrophosphination of Terminal Alkybes Catlyzwed by an Iron Complex2014

    • Author(s)
      M. Itazaki, M. Kamitani, K. Katsube, C. Tamiya, H. Nakazawa, "Selective Hydrophosphination of Terminal Alkybes Catlyzwed by an Iron Complex
    • Organizer
      5th EuCheMS Chemistry Congress
    • Place of Presentation
      イスタンブール(トルコ)
    • Year and Date
      2014-08-31 – 2014-09-04
    • Related Report
      2014 Research-status Report
  • [Presentation] Selective B-O-Si Bond Formation Catalyzed by a Transition-Metal Complex2014

    • Author(s)
      M. Ito, M. Itazaki, H. Nakazawa
    • Organizer
      5th EuCheMS Chemistry Congress
    • Place of Presentation
      イスタンブール(トルコ)
    • Year and Date
      2014-08-31 – 2014-09-04
    • Related Report
      2014 Research-status Report
  • [Presentation] Transfer Hydrogenation of Alkynes and Alkenes from Isopropyl Alcohol Catalyzed by an Fe-H/Si-H Bufunctional Complex and Their Mechanistic Studies2014

    • Author(s)
      Y. Nishiguchi, M. Kamitani, R. Tada, M. Itazaki, H. Nakazawa
    • Organizer
      The XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(札幌市、北海道)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report
  • [Presentation] Single and Double Hydrophosphination of Terminal Acetylenes with Biarylphosphine Catalyzed by an Iron Complex2014

    • Author(s)
      M. Itazaki, M. Kamitani, S. Katsube, C. Tamiya, H. Nakazawa
    • Organizer
      The XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(札幌市、北海道)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report
  • [Presentation] 鉄触媒を用いた末端アルキンの選択的モノヒドロホスフィン化反応2014

    • Author(s)
      板崎真澄、勝部伸哉、神谷昌宏、中沢 浩
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 鉄シリル錯体とアミド化合物 Ar2NCHE (E = S, O) による鉄カルベン錯体の合成と構造2014

    • Author(s)
      板崎真澄、筈谷真企、伊藤昌輝、橋本康弘、中沢 浩
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Selective Hydrophosphination of Therminal Arylacetylenes Catalyzed by an Iron Complex2013

    • Author(s)
      板崎真澄、神谷昌宏、勝部伸哉、田宮千裕、中沢 浩
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 8族遷移金属-インジウム結合の考察:錯体の合成と構造2013

    • Author(s)
      伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      錯体化学会第63回討論会
    • Place of Presentation
      琉球大学
    • Related Report
      2013 Research-status Report
  • [Presentation] モリブデン錯体を触媒としたボリルシリルエーテル合成反応2013

    • Author(s)
      伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      第40回有機典型元素化学討論会
    • Place of Presentation
      近畿大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Syntheses and Structures of Complexes Containing Group 8 Transition-Metal-Indium Bond(s)2013

    • Author(s)
      伊藤昌輝、板崎真澄、中沢 浩
    • Organizer
      第2回日仏錯体化学シンポジウム
    • Place of Presentation
      奈良市東大寺総合文化センター
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Platinum Complexes with 1,1ʹ-Ferrocenedichalcogenato Ligand and Their Reactivity2013

    • Author(s)
      板崎真澄、井関柾登、伊藤昌輝、中沢 浩
    • Organizer
      第2回日仏錯体化学シンポジウム
    • Place of Presentation
      奈良市東大寺総合文化センター
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis and Structure of Iron Carbene Complexes2013

    • Author(s)
      板崎真澄、筈谷真企、伊藤昌輝、橋本康弘、中沢 浩
    • Organizer
      第2回日仏錯体化学シンポジウム
    • Place of Presentation
      奈良市東大寺総合文化センター
    • Related Report
      2013 Research-status Report
  • [Book] Iron Catalysis II2015

    • Author(s)
      Masumi Itazaki, Hiroshi Nakazawa
    • Total Pages
      361
    • Publisher
      Springer
    • Related Report
      2015 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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