Development of Helically Chiral Polymers Based on the Condensation of Arylboronic Acids with Diamines

2014 Fiscal Year Final Research Report

• Project/Area Number: 24750105
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Polymer chemistry
• Research Institution: Kyoto University
• Principal Investigator: YAMAMOTO Takeshi 京都大学, 工学(系)研究科(研究院), 助教 (20624349)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: 合成化学 / らせん / Ｃ－Ｈ活性化 / ボリル化 / オリゴアレーン / 保護基 / 配向基

Outline of Final Research Achievements

In this study, we established precise synthesis and helical chirality induction of ortho-linked oligo(naphthalene-2,3-diyl)s. Oligo(naphthalene-2,3-diyl)s with a terminal boronyl group were synthesized by iterative Suzuki-Miyaura cross-coupling of 3-iodo-2-naphthylboronic acid bearing 1,8-diaminonaphthalene as a protecting group on the boron atom. Hydrolysis of the protecting group and subsequent condensation with chiral diols gave helically chiral oligo(naphthalene-2,3-diyl)s. Furthermore, using 2-pyrazolylaniline as a removable directing group on the boron atom, we developed an efficient synthetic method for 1,2-diboryl arenes via iridium-catalyzed aromatic ortho-C-H borylation of arylboronic acids.

Free Research Field

有機合成