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Strategy development for rapid increase in complexity and diversity of phosphorus-containing polyaromatic compounds

Research Project

Project/Area Number 26620086
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

TOBISU Mamoru  大阪大学, 工学(系)研究科(研究院), 准教授 (60403143)

Project Period (FY) 2014-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywords均一系触媒反応 / π共役化合物 / クロスカップリング / リン化合物 / π共役系化合物
Outline of Final Research Achievements

To establish robust synthetic strategy to rapidly increase both complexity and diversity of pai-conjugated compounds, the following investigation has been performed. 1) Catalytic construction of pai-conjugated scaffold: Compared to phosphorus-linked biaryl compounds (i.e., phosphole), the corresponding six-membered phophacycles (phosphorus-bridged biaryl ether or amine) are less explored, especially in terms of their catalytic synthesis. Our newly developed cyclization method via C-P bond cleavage has successfully been applied to the synthesis of polyannulated six-membered phosphacycles. 2) Late stage functionalization of pai-conjugated molecules via C-O bond cleavage: In this study, a robust methoxy group is demonstrated to serve as a versatile handle for the introduction of an alkynyl group to siloles, ferrocenes and polyaromatics at the late stage of synthesis by using a nickel-based catalyst. The flexible synthesis of dibenzochrysene was also accomplished.

Report

(2 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • Research Products

    (2 results)

All 2015

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results)

  • [Journal Article] Palladium-Catalyzed Synthesis of Six-Membered Benzofuzed Phosphacycles via Carbon-Phosphorus Bond Cleavage2015

    • Author(s)
      Katsuaki Baba, Mamoru Tobisu, and Naoto Chatani
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 1 Pages: 70-73

    • DOI

      10.1021/ol503252t

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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

URL: 

Published: 2014-04-04   Modified: 2016-06-03  

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