Room-Temperature ZnBr2-Catalyzed Regioselective 1,6-Hydroarylation of Electron-Rich Arenes to para-Quinone Methides: Synthesis of Unsymmetrical Triarylmethanes

Biquan Xiong (Corresponding Author), Lulu Si, Longzhi Zhu (Corresponding Author), Rong Wu, Yu Liu, Weifeng Xu, Fan Zhang, Ke Wen Tang, Wai Yeung Wong (Corresponding Author)

Research output: Journal article publicationJournal articleAcademic researchpeer-review

1 Citation (Scopus)

Abstract

A mild and efficient Zn(II)-catalyzed regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with electron-rich arenes protocol is reported. A variety of electron-rich arenes and para-quinone methides are well tolerated under mild conditions, delivering a broad range of triarylmethanes in good to excellent yields. The present method also works well for the hydroarylation of p-QMs with other nucleophiles, such as aniline, indole and phenol derivatives, offering the corresponding triarylmethanes with good yields under the standard conditions. The possible mechanism for the formation of C(sp3)−C(sp2) bonds in hydroarylation reactions has been explored by step-by-step control experiments, and the reaction may follow a second-order manner in a chemical kinetic study.

Original languageEnglish
Article numbere202201156
JournalChemistry - An Asian Journal
Volume18
Issue number3
Early online date12 Dec 2022
DOIs
Publication statusE-pub ahead of print - 12 Dec 2022

Keywords

  • Electron-rich arenes
  • High atomic economy
  • Hydroarylation
  • Lewis acids synergetic catalysis
  • para-Quinone methides

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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