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Syntheses of Organoboron compounds by Novel Carbon Boron Bond-Forming Reactions

Research Project

Project/Area Number 11650880
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKitami Institute of Technology

Principal Investigator

MASUDA Yuzuru  Faculty of Engineering Kitami Institute of Technology Professor, 工学部, 教授 (10003188)

Co-Investigator(Kenkyū-buntansha) MURATA Miki  Faculty of Engineering Kitami Institute of Technology Research Assistant, 工学部, 助手 (40271754)
WATANABE Shinji  Faculty of Engineering Kitami Institute of Technology Associate Professor, 工学部, 助教授 (10240491)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥2,700,000 (Direct Cost: ¥2,700,000)
Fiscal Year 2000: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1999: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsPalladium Catalyst / Hydroboranes / Borylation / Organic Halides / Organoboranes
Research Abstract

We recently developed a novel transition metal-catalyzed borylation or silylation reaction of aryl halides utilizing dialkoxyboranes and trialkoxysilanes, respectively, as metalating reagents. Then, the selective borylation of aryl electrophiles was extended to a reaction of other substrates.
Cyclic alkenyl halides or triflatess were borylated with pinacolborane in the presence of NEt_3 and a catalytic amount of PdCl_2 (dppf) and AsPh_3 to afford the corresponding cycloalkenylboronates, which are not available by this conventional addition technique, in good yields.
Although aryl and alkenyl halides couple with pinacolborane successfully in the presence of a palladium catalyst to give organoboranes, the coupling reaction of allyl halides by using Pd(dba)_2 catalyst gave only reduced hydrocarbons. Allyl halides were borylated in the presence of NEt_3 and a catalytic amount of Pt(dba)_2 and AsPh_3 to afford regio- and stereodefined (E)-allylboranes in good yields.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Miki Murata et al.: "Synthesis of Alkenylboronates via Palladium-Catalyzed Borylation of Alkeny Triflates (or Iodides) with Pinacolborane"Synthesis. 778-780 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Miki Murata et al.: "Regio-and Stereoselective Synthesis of Allylboranes via Platinum(0)-Catalyzed Borylation of Allyl Halides with Pinacolborane"Tetrahedron Letters. Vol.41. 5877-5880 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Murata et al.: "Synthesis of Alkenylboronates via Palladium-Catalyzed Borylation of Alkeny Triflates (or Iodides) with Pinacolborane"Synthesis. 778-780 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Murata et al.: "Regio- and Stereoselective Synthesis of Allylboranes via Platinum (O)-Catalyzed Borylation of Allyl Halides with Pinacolborane"Tetrahedron Letters. vol.41. 5877-5880 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Miki Murata et al.: "Synthesis of Alkenylboronates via Palladium-Catalyzed Borylation of Alkeny Triflates (or Iodides) with Pinacolborane"Synthesis. 778-780 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Miki Murata et al.: "Regio-and Stereoselective Synthesis of Allylboranes via Platinum (O)-Catalyzed Borylation of Allyl Halides with Pinacolborane"Tetrahedron Letters. 5877-5880 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Miki Murata et al.: "Synthesis of Alkenylboronates via Palladium-Catalyzed Borylation of Alkeny Triflates (or Iodides) with Pinacolborane"SYNTHESIS. (印刷中).

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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