Synthesis of benzylpalladium complexes through C-O bond cleavage of benzylic carboxylates: Development of a novel palladium-catalyzed benzylation of olefins

Hirohisa Narahashi, Isao Shimizu*, Akio Yamamoto

*この研究の対応する著者

研究成果: Article査読

55 被引用数 (Scopus)

抄録

Benzylic carboxylates were found to react with Pd(0) complexes bearing tertiary phosphines to give benzylpalladium(II) carboxylate complexes with cleavage of the benzyl-oxygen bond. The benzylpalladium complexes having the trifluoroacetato ligand react with olefins such as ethyl acrylate to give olefin benzylation products. On the basis of these studies a novel palladium-catalyzed benzylation of olefins was developed without using organic halides as the starting materials. The method has another advantage of requiring no base as in the conventional Mizoroki-Heck process using organic halides. The catalytic cycle is proposed to be constituted of elementary processes of (a) oxidative addition of a benzyl carboxylate with C-O bond cleavage to a Pd(0) complex to give a benzylpalladium carboxylate, (b) olefin insertion into the benzylpalladium bond to give an alkylpalladium complex, and (c) β-H abstraction to liberate the benzylated olefin.

本文言語English
ページ(範囲)283-296
ページ数14
ジャーナルJournal of Organometallic Chemistry
693
2
DOI
出版ステータスPublished - 2008 1 15

ASJC Scopus subject areas

  • 化学工学(その他)
  • 材料科学(その他)
  • 材料化学
  • 物理化学および理論化学
  • 有機化学
  • 無機化学
  • 生化学

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