Quadruple Role of Pd Catalyst in Domino Reaction Involving Aryl to Alkyl 1,5-Pd Migration to Access 1,9-Bridged Triptycenes

Takayuki Iwata, Satoru Kumagai, Tatsuro Yoshinaga, Masato Hanada, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo

研究成果: ジャーナルへの寄稿学術誌査読

3 被引用数 (Scopus)

抄録

A Pd-catalyzed domino reaction of 1,8,13-tribromo-9-methoxytriptycenes is reported. Under conventional Suzuki coupling conditions, the triptycenes underwent multiple transformations to give 1,9-bridged triptycenes. Based on mechanistic investigations, a single Pd catalyst functions as Pd0, PdII and PdIV species to catalyze four distinct processes: (1) aryl to alkyl 1,5-Pd migration, (2) intramolecular arylation, (3) homocoupling of phenylboronic acid and (4) Suzuki coupling. DFT calculations revealed that 1,5-Pd migration likely proceeds via both concerted PdII and stepwise PdIV routes. Asymmetric synthesis of the chiral triptycenes, as well as optical resolution, and further transformation are also reported.

本文言語英語
ページ(範囲)11548-11553
ページ数6
ジャーナルChemistry - A European Journal
27
45
DOI
出版ステータス出版済み - 8月 11 2021

!!!All Science Journal Classification (ASJC) codes

  • 触媒
  • 有機化学

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