Development of New Catalytic Reactions Directed to Straightforward Synthesis

• Project Area: Molecule Activation Directed toward Straightforward Synthesis
• Project/Area Number: 22105001
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Osaka 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): NAKAO Yoshiaki 京都大学, 大学院工学研究科, 教授 (60346088) ; MURAKAMI Masahiro 京都大学, 大学院工学研究科, 教授 (20174279) ; IWASAWA Nobuharu 東京工業大学, 大学院理工学研究科, 教授 (40168563) ; ITOH Shinobu 大阪大学, 大学院工学研究科, 教授 (30184659) ; KAWAGUCHI Hiroyuki 東京工業大学, 大学院理工学研究科, 教授 (20262850) ; MASHIMA Kazushi 大阪大学, 大学院基礎工学科, 教授 (70159143) ; GOTO Kei 東京工業大学, 大学院理工学研究科, 教授 (70262144) ; SHIRO Yoshitsugu 国立研究開発法人, 理化学研究所, 主任研究員 (70183051) ; HAYASHI Takashi 大阪大学, 大学院工学研究科, 教授 (20222226)
• Project Period (FY): 2010-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥81,510,000 (Direct Cost: ¥62,700,000、Indirect Cost: ¥18,810,000); Fiscal Year 2015: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2014: ¥15,470,000 (Direct Cost: ¥11,900,000、Indirect Cost: ¥3,570,000); Fiscal Year 2013: ¥16,250,000 (Direct Cost: ¥12,500,000、Indirect Cost: ¥3,750,000); Fiscal Year 2012: ¥17,030,000 (Direct Cost: ¥13,100,000、Indirect Cost: ¥3,930,000); Fiscal Year 2011: ¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000); Fiscal Year 2010: ¥11,960,000 (Direct Cost: ¥9,200,000、Indirect Cost: ¥2,760,000)
• Keywords: 直截分子変換 / 分子活性化 / 結合活性化 / 反応活性種 / 反応場 / 直截的分子変換

Outline of Final Research Achievements

The project overachieved. A number of papers publishedｄ in these five years was approximately1 400 and there were many patent applications. We also played an important and active role in advancing with the development of young researchers: for examples, sending a young professors abroad for a lecture trip and holding a seminar for young researchers. We also encouraged the promotion of joint R&D between academia and private companies. Weissued News Letter monthly and a total number of News Letter we issued was 50. An open symposium for public was held twice a year. We also organized International Symposium on Molecular Activation every year and supported symposia and seminars related to molecular activation.

Research Products

• [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 Group (2015)
  • 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
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives (2014)
  • 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
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance (2014)
  • Author(s): Aihara, Y.; Chatani, N.
  • Journal Title: J. Am. Chem. Soc. Volume: 136 Issue: 3 Pages: 898-901
  • DOI: 10.1021/ja411715v
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Nickel-Catalyzed Direct Alkylation of CH Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance (2013)
  • Author(s): Aihara, Y.; Chatani, N.
  • Journal Title: J. Am. Chem. Soc. Volume: 135 Issue: 14 Pages: 5308-5311
  • DOI: 10.1021/ja401344e
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Ruthenium-Catalyzed Cyclocarbonylation of Aliphatic Amides through the Regioselective Activation of Unactivated C(sp3)-H Bonds (2013)
  • 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
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds Using Bidentate Directing Groups (2013)
  • Author(s): Rouquet, G.; Chatani, N.
  • Journal Title: Angew. Chem. Int. Ed. Volume: 52 Issue: 45 Pages: 11726-11743
  • DOI: 10.1002/anie.201301451
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Palladium-Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines via Cleavage of Carbon-Hydrogen and Carbon-Phosphorus Bonds (2013)
  • Author(s): Katsuaki Baba
  • Journal Title: Angewandte Chemie International Edition Volume: 52 Issue: 45 Pages: 11892-11895
  • DOI: 10.1002/anie.201307115
  • Peer Reviewed
• [Journal Article] Modular Synthesis of Phenanthridine Derivatives via Oxidative Cylization of 2-Isocyanobiphenyls with Organoboron Reagents (2012)
  • Author(s): Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N.
  • Journal Title: Angew. Chem. Int. Ed. Volume: 51 Issue: 45 Pages: 11363-12366
  • DOI: 10.1002/anie.201206115
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Carbon-Silicon Bond Activation for Synthesis of Benzosilole Derivatives (2012)
  • Author(s): Masahiro Onoe, Katsuaki Baba, Yoonjoo Kim, Yusuke Kita, Mamoru Tobisu, Naoto Chatani
  • Journal Title: Journal of the American Chemical Society Volume: 134 Issue: 47 Pages: 19477-19488
  • DOI: 10.1021/ja3096174
  • Peer Reviewed
• [Journal Article] Highly Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds by Ruthenium Carbonyl (2011)
  • 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
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives (2011)
  • Author(s): 阿野勇介・鳶巣守・茶谷直人
  • Journal Title: Journal of the American Chemical Society Volume: 133 Issue: 33 Pages: 12984-12986
  • DOI: 10.1021/ja206002m
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Chelation-Assisted Transformations Involving Ortho C-H Bond Activation : Regioselective Oxidative Cycloaddition of Aromatic Amides to Alkynes (2011)
  • 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
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Amination of Aryl Carboxylates via the Cleavage of Aryl-Oxygen Bonds (2010)
  • Author(s): Naoto Chatani, et al
  • Journal Title: Angewandte Chemie International Edition Volume: 49 Pages: 2929-2932
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Alkenylation of Nitriles via Silicon-Assisted C-CN Bond Cleavage (2010)
  • Author(s): Naoto Chatani, et al
  • Journal Title: Organic Letters Volume: 12 Pages: 1864-1867
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Cyclization of Difluoro-Substituted 1,6-Enynes with Organozinc Reagents (2010)
  • Author(s): Naoto Chatani, et al
  • Journal Title: Angewandte Chemie International Edition Volume: 49 Pages: 8717-8720
  • Peer Reviewed
• [Presentation] A New Stage of Catalytic Functionalization of C-H Bonds (2015)
  • Author(s): N. Chatani
  • Organizer: Pure and Applied Chemistry International Conference 2015
  • Place of Presentation: Bangkok, Thailand
  • Year and Date: 2015-01-21
  • Int'l Joint Research / Invited
• [Presentation] C-H Functionalization Utilizing New Chelation System (2014)
  • Author(s): N. Chatani
  • Organizer: 2nd International Symposium on C-H Activation
  • Place of Presentation: Rennes, France
  • Year and Date: 2014-06-30
  • Int'l Joint Research / Invited
• [Presentation] Direct Functionalization of C-H Bonds Utilizing New Chelation System (2014)
  • Author(s): N. Chatani
  • Organizer: The 49th Burgenstock Conference
  • Place of Presentation: Brunnen, Switzerland
  • Year and Date: 2014-05-04
  • Int'l Joint Research / Invited
• [Presentation] New Chelation-Assisted Transformations of C-H Bonds (2013)
  • Author(s): Naoto Chatani
  • Organizer: The 17th Sigma Aldrich Organic Synthesis Meeting
  • Place of Presentation: Blankenberge, Belgium
  • Year and Date: 2013-12-06
  • Invited
• [Presentation] New Chelation-Assisted Transformations of C-H Bonds (2013)
  • Author(s): Naoto Chatani
  • Organizer: The 11th International Symposium on Organic Reaction (ISOR-11)
  • Place of Presentation: Taipei, Taiwan
  • Year and Date: 2013-11-19 – 2013-11-22
  • Invited
• [Presentation] New Chelation-Assisted Transformations of C-H Bonds (2013)
  • Author(s): Ｎａｏｔｏ Ｃｈａｔａｎｉ
  • Organizer: The Nagoya Medal of Organic Chemistry 2013
  • Place of Presentation: Nagoya, Japan
  • Year and Date: 2013-11-07
  • Invited
• [Presentation] Transformations of C-H Bonds through a Bidentate Directed C-H Activation (2013)
  • Author(s): Naoto Chatani
  • Organizer: 245th American Chemical Society National Meeting
  • Place of Presentation: New Orleans, USA
  • Year and Date: 2013-04-09 – 2013-04-10
  • Invited
• [Presentation] Chelation-Assisted Transformations Involving C-H Bond Activation (2012)
  • Author(s): N. Chatani
  • Organizer: (3) 18th International Symposium on Homogeneous Catalysis (ISHC-XVIII)
  • Place of Presentation: Toulouse, France
  • Invited
• [Presentation] Transformations Involving C-H Bond Activation Utilizing a Bidentate Directing System (2012)
  • Author(s): N. Chatani
  • Organizer: (5) 7th Asian-European Symposium on Metal-Mediated Efficient Organic Synthesis
  • Place of Presentation: Tarragona, Spain
  • Invited
• [Presentation] Catalytic Reactions Involving Activation of Unreactive Bonds (2012)
  • Author(s): N. Chatani
  • Organizer: The 6th Kansai-CMDS Meeting on OMCOS
  • Place of Presentation: Sorak Mt., Korea
  • Invited
• [Presentation] Chelation-Assisted Transformations Involving C-H Bond Activation (2012)
  • Author(s): N. Chatani
  • Organizer: The 1st International Symposium on C-H Activation
  • Place of Presentation: Beijing, China
  • Invited
• [Presentation] Catalytic Transformations Involving Activation of C-H Bonds Utilizing a Bidentate Directing System (2011)
  • 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
• [Presentation] Regioselective Carbonylation of Unactivated C(sp^3)-H Bonds in Aliphatic Amides (2011)
  • 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: 2011-10-01
• [Presentation] Catalytic Transformations Involving Activation of C-H Bonds (2011)
  • 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
• [Presentation] Catalytic Transformations Involving Activation of Unreactive Bonds (2010)
  • Author(s): Naoto Chatani
  • Organizer: 3^<rd> Peking University-Elli Lilly Symposium
  • Place of Presentation: Beijing, China(招待講演)
  • Year and Date: 2010-10-26
• [Book] Cleavage of Carbon-Carbon Single Bonds by Transition Metals (2015)
  • Author(s): M. Murakami and N. Chatani (Editors)
  • Publisher: Wiley-VCH
• [Remarks] http://www.chem.eng.osaka-u.ac.jp/~muraken/
• [Remarks] 分子活性化
  • URL: http://www.molecular-activation.jp/
• [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/publications/index.html
• [Remarks]
  • URL: http://www.molecular-activation.jp/
• [Funded Workshop] Murai Symposium (2014)
  • Place of Presentation: 奈良
  • Year and Date: 2014-10-29
• [Funded Workshop] OM&Cat-2014 (2014)
  • Place of Presentation: 奈良
  • Year and Date: 2014-10-26
• [Funded Workshop] Conference on C-C Bond Cleavage (2014)
  • Place of Presentation: 京都
  • Year and Date: 2014-10-24