Grant-in-Aid for Scientific Research on Innovative AreasPrecise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions

Takashi Nishikata » Japanese

Affiliation Graduate School of Sciences and Technology for Innovation, Yamaguchi University
Position Associate professor
Contact Email
HP http://nisikata.chem.yamaguchi-u.ac.jp/
Speciality Synthetic organic chemistry, organometallic chemistry, radical chemistry
Keyword Alkylation, Arylation, radical reaction, C-H functionalization
Institute CSJ, SSOJ, ACS

Abstract

◆Project:
The formation of a radical reaction field near an aromatic C-H bond for extremely difficult alkylations

◆Abstract:
The aromatic C-H bond functionalization is one of symbolic research topics in extremely difficult conversion reactions. The aromatic C-H arylations and 1-alkenylations have been well established in the last two decades. On the other hand, aromatic C-H alkylations (especially functionalized tertiary-alkylations) have not yet been well established. During the course of our radical tertiary-alkylation studies using alpha-bromocarbonyls and copper catalyst, we discovered that our methodology is suitable for the aromatic C-H alkylations, in which short-life time alkyl radicals react with aromatic C-H bonds to produce the corresponding tertiary-alkylated arenes. In this research, we try to establish “radical reaction field near aromatic C-H bond”.

Achievement

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Original papers

  • "Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons"
    Hirata, G.; Yamane, Y.; Tsubaki, N.; Hara, R.; *Nishikata, T.
    Beilstein J. Org. Chem., 2020, 16, 502-508
  • "The Mizoroki-Heck reaction with internal olefins: Reactivities and stereoselectivities"
    Yusei Nakashima, Goki Hirata, Tom D Sheppard, Takashi Nishikata
    Asian J. Org. Chem., 2020, 9, 480-491
  • "Construction of vicinal quaternary carbons via Cu-catalyzed dearomative radical addition"
    Naoki Tsuchiya, Takashi Nishikata
    Chem. Lett., 2019, 48, 718-721
  • "Iron-Enhanced Reactivity of Radicals Enables C−H Tertiary
    Alkylations for Construction of Functionalized Quaternary Carbons"
    Yu Yamane, Kohei Yoshinaga, Michinori Sumimoto, and Takashi Nishikata*
    ACS Catal., 2019, 4(9), 1757-1762
  • "Ppm Cu catalyst enables tert-alkylation followed by C-H cyclization to synthesize substituted oxindoles"
    K. Yoshinaga, N. Tsubaki, Y. Murata, N. Yushi, T. Nishikata*
    ACS omega, 2018, 3, 9020-9026
  • "Radical-Organometallic Hybrid Reaction System Enabling Couplings between Tertiary-Alkyl Groups and 1‑Alkenyl Groups"
    K. Nakamura, R. Hara, Y. Sunada, T. Nishikata*
    ACS Catal., 2018, 8, 6791-6795

Conference

  • PSRC-9
    "The transformations of α-bromocarbonyls", Invited Lecture
    Takashi Nishikata
    6/16/2019~6/21/2019, California, USA

National Conference

  • 第66回有機金属化学討論会
    "鉄触媒β-アルキルスチレンへの選択的第三級アルキル置換反応開発", ポスター発表
    中島悠成、松本淳希、平田剛輝、西形孝司
    9/14/2019~9/16/2019, 東京
  • 第66回有機金属化学討論会
    "Sterically Congested Cross Coupling Reaction for Amino Acid Synthesis", 口頭発表
    Ryo Yazaki, Yohei Matsumoto, Jun Sawamura, Yumi Murata, Takashi Nishikata, and Takashi Ohshima
    9/14/2019~9/19/2019, 東京
  • 第31回若手研究者のためのセミナー
    "第三級炭素上での反応化学:立体障害に打ち勝つ多彩な合成方法論", 招待講演
    西形孝司
    8/31/2019~8/31/2019, 福岡
  • 第29回福岡万有シンポジウム
    "銅触媒脱芳香族付加反応による室温下での隣接第四級炭素構築法開発", ポスター発表
    土屋直輝、西形孝司
    5/25/2019~5/25/2019, 福岡
  • 第13回プロセス化学ラウンジ
    "銅触媒で制御する3級アルキル化反応の化学", 招待講演
    西形孝司
    11/30/2018~11/30/2018, 静岡
  • 若手研究者のための有機合成化学札幌セミナー
    "α-ブロモカルボニル化学の世界", 招待講演
    西形孝司
    11/8/2018~11/8/2018, 北海道
  • CSJ化学フェスタ
    "2つの活性種を駆使して立体障害に挑む反応化学", 招待講演
    西形孝司
    10/23/2018~10/23/2018, 東京
  • 第46回オルガノメタリックセミナー
    "銅触媒による活性種制御に基づいた分岐型反応開発", 招待講演
    西形孝司
    10/5/2018~10/5/2018, 広島
  • 第35回有機合成化学セミナー
    "α-ブロモカルボニルを第3級アルキル源とする多彩な合成化学", 招待講演
    西形孝司
    9/18/2018~9/20/2018, 山形
  • 中国四国地区錯体化学研究会
    "銅錯体とアルキルラジカル種の反応による立体的に込み合った分子合成", 招待講演
    西形孝司
    4/28/2018~4/28/2018, 高知

Award

  • 「Thieme Chemistry Journals Award」
    受賞者:Takashi Nishikata
    贈呈元:Thieme
    受賞日:1/7/2019

Media

  • ACS Catal., カバーピクチャ
    「Radical-Organometallic Hybrid Reaction System Enabling Couplings between Tertiary-Alkyl Groups and 1‑Alkenyl Groups」
    K. Nakamura, R. Hara, Y. Sunada, T. Nishikata*, 8/4/2018
    PDF File
  • 科学新聞, 雑誌記事
    「1つの反応系で2つの活性種を使用可能」
    K. Nakamura, R. Hara, Y. Sunada, T. Nishikata*, 6/29/2018
    PDF File
  • 化学工業日報, 新聞
    「新クロスカップリング」
    K. Nakamura, R. Hara, Y. Sunada, T. Nishikata*, 6/19/2018