Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Koji Nemoto, Shinya Tanaka, Megumi Konno, Satoru Onozawa, Masafumi Chiba, Yuuki Tanaka, Yosuke Sasaki, Ryo Okubo, Tetsutaro Hattori

研究成果: Article査読

43 被引用数 (Scopus)

抄録

Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.

本文言語English
ページ(範囲)734-745
ページ数12
ジャーナルTetrahedron
72
5
DOI
出版ステータスPublished - 2016 2月 4

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル