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Development of Catalytic reactions Involving Activation of Unreactive Bonds

Planned Research

Project AreaMolecule Activation Directed toward Straightforward Synthesis
Project/Area Number 22105002
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionOsaka University

Principal Investigator

CHATANI Naoto  大阪大学, 工学(系)研究科(研究院), 教授 (30171953)

Co-Investigator(Renkei-kenkyūsha) FUKUMOTO Yoshiya  大阪大学, 大学院工学研究科, 准教授 (50273595)
TOBISU Mamoru  大阪大学, 大学院工学研究科, 准教授 (60403143)
Project Period (FY) 2010-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥120,510,000 (Direct Cost: ¥92,700,000、Indirect Cost: ¥27,810,000)
Fiscal Year 2014: ¥17,420,000 (Direct Cost: ¥13,400,000、Indirect Cost: ¥4,020,000)
Fiscal Year 2013: ¥18,330,000 (Direct Cost: ¥14,100,000、Indirect Cost: ¥4,230,000)
Fiscal Year 2012: ¥19,110,000 (Direct Cost: ¥14,700,000、Indirect Cost: ¥4,410,000)
Fiscal Year 2011: ¥18,980,000 (Direct Cost: ¥14,600,000、Indirect Cost: ¥4,380,000)
Fiscal Year 2010: ¥46,670,000 (Direct Cost: ¥35,900,000、Indirect Cost: ¥10,770,000)
Keywords炭素-水素結合活性化 / 炭素-酸素結合活性化 / 炭素-窒素結合活性化 / 炭素-リン結合活性化 / 炭素-硫黄結合活性化 / 分子活性化 / キレーション / 配向基 / 炭素-炭素結合活性化 / 炭素ー酸素結合活性化 / ルテニウム / ニッケル / 炭素-水素結合活性化 / 炭素-酸素結合活性化 / 炭素-窒素結合活性化 / 炭素-フッ素結合活性化 / 炭素-炭素結合活性化 / 炭素-酸素合活性化 / 飽和炭素-水素結合 / カルボニル化 / ボリル化
Outline of Final Research Achievements

A new type of C-H functionalization reactions utilizing an N,N-bidentate chelation system has been developed. It was found that Ni/8-aminoquinoline directing group is reliable system for developing the Ni-catalyzed C-H functionalizations. In addition, some catalytic reactions using ruthenium and rhodium chlorides have been successfully developed.
After the examination of the effect of NHC ligands on the efficiency of C-O bond activation, it was found that ICy shows a high catalytic activity. The use of ICy led to the development of new reactions, which cannot achieve by using conventional common ligands.

Report

(6 results)
  • 2015 Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (48 results)

All 2015 2014 2013 2012 2011 2010 Other

All Journal Article (27 results) (of which Peer Reviewed: 27 results,  Acknowledgement Compliant: 13 results,  Open Access: 3 results) Presentation (18 results) (of which Int'l Joint Research: 5 results,  Invited: 14 results) Remarks (3 results)

  • [Journal Article] Nickel-Catalyzed Alkynylation of Anisoles via C-O Bond Cleavage2015

    • Author(s)
      Tobisu, M.; Takahira, T.; Ohtsuki, A.; Chatani, N.
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 3 Pages: 680-683

    • DOI

      10.1021/ol503707m

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Borylation of Aryl 2-Pyridyl Ethers through Cleavage of the Carbon-Oxygen Bond: Borylative Removal of the Directing Group2015

    • Author(s)
      Hirotaka Kinuta, Mamoru Tobisu, Naoto Chatani
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 4 Pages: 1593-1600

    • DOI

      10.1021/ja511622e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group2015

    • Author(s)
      Yoshinori AIhara, Jendrick Wuelbern, Naoto Chatani
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 88 Issue: 3 Pages: 438-446

    • DOI

      10.1246/bcsj.20140387

    • NAID

      130004801839

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Palladium(II)-Catalyzed ortho-C(sp2)-H Arylation/Alkylation of N-benzoyl α-amino Ester Derivatives2014

    • Author(s)
      L. C. Misal Castro and N. Chatani
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 16 Pages: 4548-4553

    • DOI

      10.1002/chem.201304978

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-Catalyzed Reductive and Borylative Cleavage of Aromatic Carbon-Nitrogen Bonds in N-Aryl Amides and Carbamates2014

    • Author(s)
      M. Tobisu, K. Nakamura, and N. Chatani
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 15 Pages: 5587-5590

    • DOI

      10.1021/ja501649a

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Theoretical Studies of Rhodium-Catalyzed Borylation of Nitriles through Cleavage of Carbon-Cyano Bonds2014

    • Author(s)
      Hirotaka Kinuta, Hiroaki Takahashi, Mamoru Tobisu, Seiji Mori, and Naoto Chatani
    • Journal Title

      Bull Chem Soc Jpn

      Volume: 87 Issue: 6 Pages: 655-669

    • DOI

      10.1246/bcsj.20130332

    • NAID

      130004059118

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Rhodium-Catalyzed Alkylation of C-H Bonds in Aromatic Amides with α,β-Unsaturated Esters2014

    • Author(s)
      Kaname Shibata and Naoto Chatani
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 19 Pages: 5148-5151

    • DOI

      10.1021/ol502500c

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives2014

    • Author(s)
      Yoshinori AIhara, Mamoru Tobisu, Yoshiya Fukumoto, Naoto Chatani
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 44 Pages: 15509-15512

    • DOI

      10.1021/ja5095342

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 1,3-Dicyclohexylimidazol-2-ylidene as a Superior Ligand for the Nickel-Catalyzed Cross-Couplings of Aryl and Benzyl Methyl Ethers with Organoboron Reagents2014

    • Author(s)
      M. Tobisu, A. Yasutome, H. Kinuta, K. Nakamura, and N. Chatani
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 21 Pages: 5572-5575

    • DOI

      10.1021/ol502583h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides with Diaryliodonium Salts in the presence of a Nickel Catalyst2014

    • Author(s)
      Miki Iyanaga, Yoshinori AIhara, Naoto Chatani
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 24 Pages: 11933-11939

    • DOI

      10.1021/jo501691f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance2014

    • Author(s)
      Aihara, Y.; Chatani, N.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 3 Pages: 898-901

    • DOI

      10.1021/ja411715v

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ruthenium-Catalyzed Ortho C-H Bond Alkylation of Aromatic Amides with α,β-Unsaturated Ketones via a Bidentate-Chelation Assistance2013

    • Author(s)
      G. Rouquet and N. Chatani
    • Journal Title

      Chem. Sci.

      Volume: 4 Issue: 5 Pages: 2201-2208

    • DOI

      10.1039/c3sc50310k

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-Catalyzed Direct Alkylation of CH Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance2013

    • Author(s)
      Aihara, Y.; Chatani, N.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 14 Pages: 5308-5311

    • DOI

      10.1021/ja401344e

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ruthenium-Catalyzed Cyclocarbonylation of Aliphatic Amides through the Regioselective Activation of Unactivated C(sp3)-H Bonds2013

    • Author(s)
      Hasegawa, N.; Shibata, K.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N.
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 22 Pages: 4466-4472

    • DOI

      10.1016/j.tet.2013.02.006

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines via Cleavage of Carbon-Hydrogen and Carbon-Phosphorus Bonds2013

    • Author(s)
      Katsuaki Baba
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 45 Pages: 11892-11895

    • DOI

      10.1002/anie.201307115

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Ru(II)-Catalyzed Chelation-Assisted Arylation of C-H Bonds with Diaryliodonium Salts2013

    • Author(s)
      J. S. Ho, L. C. M. Castro, Y. Aihara, M. Tobisu, and N. Chatani
    • Journal Title

      Asian J. Org. Chem.

      Volume: 3 Issue: 12 Pages: 48-51

    • DOI

      10.1002/ajoc.201300188

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ruthenium-Catalyzed Direct Arylation of C-H Bonds in Aromatic Amides Containing a Bidentate Directing Group: Significant Electronic Effects on Arylation2013

    • Author(s)
      Aihara, Y.; Chatani, N.
    • Journal Title

      Chem. Sci.

      Volume: 4 Issue: 2 Pages: 664-670

    • DOI

      10.1039/c2sc21506c

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Carbonylation of ortho C-H Bonds in Arylacetamides: C-H Bond Activation Utilizing a Bidentate-Chelation System2012

    • Author(s)
      Shibata, K.; Hasegawa, N.; Fukumoto, Y.; Chatani, N.
    • Journal Title

      ChemCatChem.

      Volume: 4 Issue: 11 Pages: 1733-1736

    • DOI

      10.1002/cctc.201200352

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Direct ortho-Alkynylation of Arenes with Chelation Assistance2012

    • Author(s)
      Tobisu, M.; Ano, Y.; Chatani, N.
    • Journal Title

      Synlett

      Volume: 23 Issue: 19 Pages: 2763-2767

    • DOI

      10.1055/s-0032-1316556

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds by Ruthenium Carbonyl2011

    • Author(s)
      Naoto Chatani, et al
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 21 Pages: 8070-8073

    • DOI

      10.1021/ja2001709

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Synthesis of Germoles via the Activation of Carbon-Germanium Bonds2011

    • Author(s)
      Naoto Chatani, et al
    • Journal Title

      Organic Letters

      Volume: 13 Pages: 3282-3284

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Switch in Stereoselectivity Caused by the Isocyanide Structure in the Rhodium-Catalyzed Silylimination of Alkynes2011

    • Author(s)
      Naoto Chatani, et al
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 26 Pages: 10014-10017

    • DOI

      10.1021/ja202881y

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Chelation-Assisted Transformations Involving Ortho C-H Bond Activation : Regioselective Oxidative Cycloaddition of Aromatic Amides to Alkynes2011

    • Author(s)
      塩田博崇・阿野勇介・相原佳典・福本能也・茶谷直人
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 38 Pages: 14952-14955

    • DOI

      10.1021/ja206850s

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Suzuki-Miyaura Reaction of Aryl Fluorides2011

    • Author(s)
      Naoto Chatani, et al
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 48 Pages: 19505-19511

    • DOI

      10.1021/ja207759e

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Reductive Cleavage of Aryl-Oxygen Bonds in Alkoxy- and Pivaloxyarenes Using Hydrosilane as a Mild Reducing Agent2011

    • Author(s)
      N.Chatani
    • Journal Title

      Chem.Commun.

      Volume: 49 Pages: 2946-2948

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Amination of Aryl Carboxylates via the Cleavage of Aryl-Oxygen Bonds2010

    • Author(s)
      N.Chatani
    • Journal Title

      Angew.Chem., Int.Ed.

      Volume: 49 Pages: 2929-2932

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Alkenylation of Nitriles via Silicon-Assisted C-CN Bond Cleavage2010

    • Author(s)
      N.Chatani
    • Journal Title

      Org.Lett

      Volume: 12 Pages: 1864-1867

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] New Chelation-Assisted Functionalization of C-H Bonds Utilizing a Bidentate Directing Group2015

    • Author(s)
      N. Chatani
    • Organizer
      13th IBN SINA International Conference on Pure and Applied Heterocyclic Chemistry
    • Place of Presentation
      Hurghada, Egypt
    • Year and Date
      2015-02-14
    • Related Report
      2014 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A New Stage of Catalytic Functionalization of C-H Bonds2015

    • Author(s)
      N. Chatani
    • Organizer
      Pure and Applied Chemistry International Conference 2015
    • Place of Presentation
      Bangkok, Thailand
    • Year and Date
      2015-01-21
    • Related Report
      2014 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalytic Functionalization of C-H Bonds Utilizing Bidentate-Chelation System2014

    • Author(s)
      N. Chatani
    • Organizer
      The 7th Kansai-CMDS Meeting on OMCOS
    • Place of Presentation
      Hirayu, Japan
    • Year and Date
      2014-10-18
    • Related Report
      2014 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] C-H Functionalization Utilizing New Chelation System2014

    • Author(s)
      N. Chatani
    • Organizer
      2nd International Symposium on C-H Activation
    • Place of Presentation
      Rennes, France
    • Year and Date
      2014-06-30
    • Related Report
      2014 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Direct Functionalization of C-H Bonds Utilizing New Chelation System2014

    • Author(s)
      N. Chatani
    • Organizer
      The 49th Burgenstock Conference
    • Place of Presentation
      Brunnen, Switzerland
    • Year and Date
      2014-05-04
    • Related Report
      2014 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] New Chelation-Assisted Transformations of C-H Bonds2013

    • Author(s)
      Naoto Chatani
    • Organizer
      The 17th Sigma Aldrich Organic Synthesis Meeting
    • Place of Presentation
      Blankenberge, Belgium
    • Year and Date
      2013-12-06
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] New Chelation-Assisted Transformations of C-H Bonds Using Bidentate Directing Group2013

    • Author(s)
      Naoto Chatani
    • Organizer
      Dr Paul Janssen Lecture Series
    • Place of Presentation
      Beerse, Belgium
    • Year and Date
      2013-12-05
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] New Chelation-Assisted Transformations of C-H Bonds2013

    • Author(s)
      Naoto Chatani
    • Organizer
      The Nagoya Medal of Organic Chemistry 2013
    • Place of Presentation
      Nagoya, Japan
    • Year and Date
      2013-11-07
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Transformations of C-H Bonds through a Bidentate Directing Group2013

    • Author(s)
      Naoto Chatani
    • Organizer
      The 16th Japan-Korea Seminar on Organic Chemistry
    • Place of Presentation
      Sendai, Japan
    • Year and Date
      2013-09-27 – 2013-09-30
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Transformations of C-H Bonds through a Bidentate Directed C-H Activation2013

    • Author(s)
      Naoto Chatani
    • Organizer
      245th American Chemical Society National Meeting
    • Place of Presentation
      New Orleans, USA
    • Year and Date
      2013-04-07 – 2013-04-11
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Cross-Coupling Reactions Involving C-O Bond Activation2012

    • Author(s)
      N. Chatani
    • Organizer
      1st International Conference on Organometallics and Catalysis (OM&Cat)
    • Place of Presentation
      Beijing, China
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Chelation-Assisted Transformations Involving C-H Bond Activation2012

    • Author(s)
      N. Chatani
    • Organizer
      The 1st International Symposium on C-H Activation
    • Place of Presentation
      Beijing, China
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Transformations Involving C-H Bond Activation Utilizing a Bidentate Directing System2012

    • Author(s)
      N. Chatani
    • Organizer
      7th Asian-EuropSymposium on Metal-Mediated Efficient Organic Synthesis
    • Place of Presentation
      Tarragona, Spain
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Chelation-Assisted Transformations Involving C-H Bond Activation2012

    • Author(s)
      N. Chatani
    • Organizer
      18th International Symposium on Homogeneous Catalysis (ISHC-XVIII)
    • Place of Presentation
      Toulouse, France
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Catalytic Transformations Involving Activation of C-H Bonds Utilizing a Bidentate Directing System2011

    • Author(s)
      Naoto Chatani
    • Organizer
      Mini-Symposium on Organometallics and Catalysis
    • Place of Presentation
      Tianjin, China(招待講演)
    • Year and Date
      2011-11-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] Catalytic Transformations Involving Activation of C-H Bonds2011

    • Author(s)
      Naoto Chatani
    • Organizer
      4th Aachen-Osaka Joint Symposium
    • Place of Presentation
      Aachen, Germany(招待講演)
    • Year and Date
      2011-09-01
    • Related Report
      2011 Annual Research Report
  • [Presentation] Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds in Aliphatic Amides2011

    • Author(s)
      Naoto Chatani
    • Organizer
      15th Japan-Korea Joint Seminar on Organic Chemistry
    • Place of Presentation
      Gyeongju, Korea(招待講演)
    • Year and Date
      2011-09-01
    • Related Report
      2011 Annual Research Report
  • [Presentation] Catalytic Transformations Involving Activation of Unreactive Bonds2010

    • Author(s)
      N.Chatani
    • Organizer
      3^<rd> Peking University-Elli Lilly Symposium
    • Place of Presentation
      北京(中国)
    • Year and Date
      2010-10-26
    • Related Report
      2010 Annual Research Report
  • [Remarks] 大阪大学工学研究科応用化学専攻茶谷研究室

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~muraken/index.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 大阪大学大学院工学研究科応用化学専攻茶谷研究室

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~muraken/

    • Related Report
      2013 Annual Research Report
  • [Remarks]

    • URL

      http://www.molecular-activation.jp/

    • Related Report
      2010 Annual Research Report

URL: 

Published: 2010-08-23   Modified: 2019-07-29  

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