Palladium-catalyzed oxirane-opening reaction with arenes via C-H bond activation

Zhen Wang, Yoichiro Kuninobu, Motomu Kanai

研究成果: Contribution to journalArticle査読

78 被引用数 (Scopus)

抄録

We achieved a palladium-catalyzed C-H activation/C-C coupling reaction between arenes with a pyridyl, aminoquinolinyl, imino, or amide directing group, and oxiranes. The reaction proceeded at room temperature without any additives and tolerated a wide variety of functional groups, and the products were obtained in good to excellent yields, even on gram scale. This is the first example of a transition-metal-catalyzed intermolecular direct coupling reaction between a C-H bond of aromatic compounds and a carbon atom of oxiranes via C-H bond activation. By using N-methoxybenzamide as a substrate, we obtained 3-substituted isochroman-1-ones in one pot. The coupling reaction proceeded with stereoretention. Kinetic isotope effect experiments suggested that C-H bond activation is the rate-determining step.

本文言語英語
ページ(範囲)6140-6143
ページ数4
ジャーナルJournal of the American Chemical Society
137
19
DOI
出版ステータス出版済み - 5 20 2015
外部発表はい

All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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