Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation

  • Shoji Shinamura
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
  • Ryusuke Sugimoto
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
  • Naoyuki Yanai
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
  • Noriko Takemura
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
  • Tomoya Kashiki
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
  • Itaru Osaka
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
  • Eigo Miyazaki
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan
  • Kazuo Takimiya
    Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan, and Emergent Molecular Function Research Team, RIKEN Advanced Science Institute, Wako, Saitama 351-0198, Japan

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説明

Selective functionalization protocols of naphtho[1,2-b;5,6-b']dithiophene (NDT3) by combining protection of the thiophene α-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomeric NDT3-based polymers with different main chain structures. The same protocol is applicable to other isomeric naphthodithiophenes (NDTs), which affords a set of key building blocks for the development of elaborated functional π-materials.

収録刊行物

  • Organic Letters

    Organic Letters 14 (18), 4718-4721, 2012-09-12

    American Chemical Society (ACS)

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