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2009 Fiscal Year Final Research Report

Synthesis and Catalytic Properties of Hemi-labile Ligands

Research Project

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Project/Area Number 18065008
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionTokyo Institute of Technology

Principal Investigator

TANAKA Masato  Tokyo Institute of Technology, 資源化学研究所, 教授 (20343163)

Co-Investigator(Kenkyū-buntansha) SANJI Takanobu  東京工業大学, 資源化学研究所, 特任准教授 (00287484)
Project Period (FY) 2006 – 2009
Keywords有機工業化学 / 合成化学 / 触媒・化学プロセス / 錯体触媒 / 配位子 / 有機リン化合物
Research Abstract

A series of ligands containing C=N and P=O moieties were created. These ligands displayed hemi-labile behaviors in palladium complexes due to interaction with oxygen of the P=O moiety and relatively high performance in ethylene oligomerization and Heck reaction. On the other hand, the foregoing observations suggested that the interaction of the oxygen in RC(O) and R2P(O) moieties with acidic promoters would enhance the reactivity. On the basis of the assumption, we were able to develop efficient addition reactions of acid chlorides or HP(O)R2 compounds with alkynes.

  • Research Products

    (29 results)

All 2009 2008 2007 2006 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (7 results) Remarks (1 results) Patent(Industrial Property Rights) (5 results)

  • [Journal Article] Synthesis of 1, 4-Dichloro-1, 3-Buta- dienes by Rhodium-Complex-Catalyzed Reaction of Terminal Alkynes with Tri- chloroacetyl Chloride2009

    • Author(s)
      Taigo Kashiwabara, Kouichirou Fuse, Takeshi Muramatsu, Masato Tanaka
    • Journal Title

      J. Org. Chem. 74

      Pages: 9433-9439

    • Peer Reviewed
  • [Journal Article] Pd-Catalyzed Addition-Carbocycli- zation of α,ω-Diynes with H-P(O)R2 Compounds2009

    • Author(s)
      Jun Kanada, Koh-ichiro Yamashita, Satish Kumar Nume, Masato Tanaka
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 6196-6199

    • Peer Reviewed
  • [Journal Article] Aggregation-Induced Emissions of Den- dritic Phosphole Oxides2009

    • Author(s)
      Takanobu Sanji, Kentaro Shiraishi, Taigo Kashiwabara, Masato Tanaka
    • Journal Title

      New J. Chem. 33

      Pages: 1680-1684

    • Peer Reviewed
  • [Journal Article] Synthesis of 1, 2-Diketones by the Transition Metal-Catalyst-Free Reaction of α-Oxo Acid Chlorides or Oxalyl Chloride with Organostannanes2009

    • Author(s)
      Taigo Kashiwabara, Masato Tanaka
    • Journal Title

      J. Org. Chem. 74

      Pages: 3958-3961

    • Peer Reviewed
  • [Journal Article] Sugar-Phosphole Oxide Conjugates as "Turn-on" Luminescent Sensors for Lectins2009

    • Author(s)
      Takanobu Sanji, Kentaro Shiraishi, Masato Tanaka
    • Journal Title

      ACS Appl. Mater. Interfaces 1

      Pages: 270-273

    • Peer Reviewed
  • [Journal Article] Rhodium-Complex-Catalyzed Addition Reactions of Chloroacetyl Chlorides to Alkynes2008

    • Author(s)
      Taigo Kashiwabara, Kohichiro Fuse, Ruimao Hua, Masato Tanaka
    • Journal Title

      Org. Lett. 10

      Pages: 5469-5472

    • Peer Reviewed
  • [Journal Article] Base-Mediated Cyclization Reaction of 2-Alkynylphenylphosphine Oxides: Synthe- sis and Photophysical Properties of Ben- zo[b]phosphole Oxides2008

    • Author(s)
      Takanobu Sanji, Kentaro Shiraishi, Taigo Kashiwabara, Masato Tanaka
    • Journal Title

      Org. Lett. 10

      Pages: 2689-2692

    • Peer Reviewed
  • [Journal Article] Synthesis and Photophysical Properties of Phosphole-Cored Dendrimers2007

    • Author(s)
      Takanobu Sanji, Kentaro Shiraishi, Masato Tanaka
    • Journal Title

      Org. Lett. 9

      Pages: 3611-3614

    • Peer Reviewed
  • [Journal Article] Ni-Catalyzed Addition Reaction of Allylic Selenides to Alkynes2007

    • Author(s)
      Koh-ichiro Yamashita, Hideaki Takeda, Taigo Kashiwabara, Ruimao Hua, Shigeru Shimada, Masato Tanaka
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 6655-6659

    • Peer Reviewed
  • [Journal Article] Palladium-complex-catalyzed regiosel- ective Markovnikov addition reaction and dehydrogenative double phosphinylation to terminal alkynes with diphenylphosphine oxide2007

    • Author(s)
      Naotomo Dobashi, Kouichiro Fuse, Takako Hoshino, Jun Kanada, Taigo Kashiwabara, Chihiro Kobata, Satish Kumar Nune, Masato Tanaka
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 4669-4673

    • Peer Reviewed
  • [Journal Article] Palladium-catalysed regioselective addition reaction of ethyl phenylphos- phinate with terminal acetylenes: Ligand- and solvent-dependent regioselectivity2007

    • Author(s)
      Satish Kumar Nune, Masato Tanaka
    • Journal Title

      Chem. Commun.

      Pages: 2858-2860

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Thioallylation of Alkynes with Allyl Phenyl Sulfides2007

    • Author(s)
      Ruimao Hua, Hideaki Takeda, Shun-ya Onozawa, Yoshimoto Abe, Masato Tanaka
    • Journal Title

      Org. Lett. 9

      Pages: 263-266

    • Peer Reviewed
  • [Journal Article] Multinuclear Palladium Compounds Con- taining Palladium Centers Ligated by Five Silicon Atoms2007

    • Author(s)
      Shigeru Shimada, Yong-Hua Li, Yoong-Kee Choe, Masato Tanaka, Ming Bao
    • Journal Title

      Tadafumi Uchimaru, Proc. Nat. Acad. Sci. 104

      Pages: 7758-7763

    • Peer Reviewed
  • [Journal Article] Decarbonylative Coupling of Fluoro- benzoyl Chlorides with Hexamethyldisilane in the Presence of Pd Complex Catalyst: Extremely Facile Decarbonylation of Pen- tafluorobenzoyl-Pd Complex Relevant to C6F5SiMe3 Formation2006

    • Author(s)
      Taigo Kashiwabara, Masato Tanaka
    • Journal Title

      Organometallics 25

      Pages: 4648-4652

    • Peer Reviewed
  • [Journal Article] Group 10 Transition-metal Complexes with Metal-silicon Bonds Derived from 1, 2-Disilylbenzenes and Bis(2-silylphen- yl)silane2006

    • Author(s)
      Shigeru Shimada, Masato Tanaka
    • Journal Title

      Coord. Chem. Rev. 250

      Pages: 991-1011

    • Peer Reviewed
  • [Journal Article] A PtIII2Si2 Four-Membered Cycle and a Dinuclear Platinum Complex Bridged by a Cyclodisiloxane Ring2006

    • Author(s)
      Shigeru Shimada, Yong-Hua Li, Maddali L.N. Rao, Masato Tanaka
    • Journal Title

      Orgaometallics 25

      Pages: 3796-3798

    • Peer Reviewed
  • [Presentation] Palladium-Catalyzed Addition-Cyclization of Diynes with Di- phenylphosphine Oxide in the Presence of Diphenylphosphinic Acid2009

    • Author(s)
      Masato Tanaka
    • Organizer
      The 14th Korea- Japan Joint Symposium on Organometallic and Coordination Chemistry
    • Place of Presentation
      Nagoya
    • Year and Date
      20091008-20091010
  • [Presentation] Disilylbenzenes: Rich Sources for Silyl-Metals of Unusual Structures2008

    • Author(s)
      Masato Tanaka
    • Organizer
      International conference on organometallic and coordination chemistry
    • Place of Presentation
      Nizhny Novgorod, Russia
    • Year and Date
      20080902-20080908
  • [Presentation] Addition Reactions of Acid Chlorides across Alkynes2008

    • Author(s)
      Masato Tanaka
    • Organizer
      The 16th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Florence, Italy
    • Year and Date
      20080706-20080711
  • [Presentation] Palladium- Catalyzed Addition-Cyclization Reaction of Diphenylphosphine Oxide with Diynes in the Presence of Phosphinic Acid2008

    • Author(s)
      Jun Kanada, Masato Tanaka
    • Organizer
      The 16th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Florence, Italy
    • Year and Date
      20080706-20080711
  • [Presentation] Catalytic Reactions of Hydrooligosilanes2008

    • Author(s)
      Masato Tanaka
    • Organizer
      he 15th International Symposium on Organosilicon Chemistry
    • Place of Presentation
      Jeju, Korea
    • Year and Date
      20080601-20080606
  • [Presentation] Selective Markovnikov Addition of P-H Bond to Terminal Alkynes and Related Reactions2007

    • Author(s)
      Masato Tanaka
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2007
    • Place of Presentation
      Singapore
    • Year and Date
      20071217-20071221
  • [Presentation] Recent progress in H-P bond addition catalysis2006

    • Author(s)
      Masato Tanaka
    • Organizer
      The 15th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Sun City, South Africa
    • Year and Date
      20060820-20060825
  • [Remarks]

    • URL

      http://www.res.titech.ac.jp/~gosei/tanaka/index.html

  • [Patent(Industrial Property Rights)] (z, z)-1, 4-ジハロ-1, 3-ブタジエン化合物の製造方法2008

    • Inventor(s)
      田中正人、柏原泰吾
    • Industrial Property Rights Holder
      東京工業大学
    • Industrial Property Number
      特許・特願2008-200200
    • Filing Date
      2008-07-04
  • [Patent(Industrial Property Rights)] 分枝鎖状アルケニルホスフィンオキシド化合物の製造方法2007

    • Inventor(s)
      田中正人、N. Satish Kumar、田中良典
    • Industrial Property Rights Holder
      東京工業大学と大八化学との共願
    • Industrial Property Number
      特許・特願2007-059928
    • Filing Date
      2007-03-09
  • [Patent(Industrial Property Rights)] 1,2-ビス(ジアリールホスフィニル)エテン骨格を有する化合物の製造方法2007

    • Inventor(s)
      田中正人、田中良典
    • Industrial Property Rights Holder
      東京工業大学と大八化学との共願
    • Industrial Property Number
      特許・特願2007-53468
    • Filing Date
      2007-03-02
  • [Patent(Industrial Property Rights)] 1,4-ジクロロ-3-ブテン-2-オン化合物及びその製造方法2007

    • Inventor(s)
      田中正人、柏原泰吾
    • Industrial Property Rights Holder
      東京工業大学
    • Industrial Property Number
      特許・特願2007-054811
    • Filing Date
      2007-02-05
  • [Patent(Industrial Property Rights)] 有機リン置換ピロール化合物及びその製造方法2007

    • Inventor(s)
      田中正人、N. Satish Kumar、田中良典
    • Industrial Property Rights Holder
      東京工業大学と大八化学との共願
    • Industrial Property Number
      特許・特願2007-31226
    • Filing Date
      2007-02-09

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Published: 2011-06-18   Modified: 2016-04-21  

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