Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids

Hirokazu Tsukamoto, Tomomi Uchiyama, Takamichi Suzuki, Yoshinori Kondo

研究成果: Article査読

72 被引用数 (Scopus)

抄録

Allylic alcohols can be used directly for the palladium(0)-catalyzed allylation of aryl- and alkenylboronic acids with a wide variety of functional groups. A triphenylphosphine-ligated palladium catalyst turns out to be most effective for the cross-coupling reaction and its low loading (less than 1 mol%) leads to formation of the coupling product in high yield. The Lewis acidity of the organoboron reagents and poor leaving ability (high basicity) of the hydroxyl group are essential for the cross-coupling reaction. The reaction process is atom-economical and environmentally benign, because it needs neither preparation of allyl halides and esters nor addition of stoichiometric amounts of a base. Furthermore, allylic alcohols containing another unsaturated carbon-carbon bond undergo arylative cyclization reactions leading to cyclopentane formation.

本文言語English
ページ(範囲)3005-3013
ページ数9
ジャーナルOrganic and Biomolecular Chemistry
6
16
DOI
出版ステータスPublished - 2008 8月 15

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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