Metal-free, Phosphoric Acid-catalyzed Regioselective 1,6-Hydroarylation of para-Quinone Methides with Indoles in Water

Biquan Xiong, Lulu Si, Yu Liu, Weifeng Xu, Tao Jiang, Fan Cao, Ke Wen Tang, Wai Yeung Wong (Corresponding Author)

Research output: Journal article publicationJournal articleAcademic researchpeer-review

Abstract

An efficient, cheap and green protocol for the highly regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with indoles at the C-3 position has been established by phosphoric acid catalysis in water under transition-metal-free reaction conditions. A wide range of indole derivatives and para-quinone methides (p-QMs) are compatible for the reaction, affording the corresponding 1,6-hydroarylation products with good to excellent yields. The possible mechanism of the reaction has been explored through step-by-step control experiments. The protocol is convenient for practical applications, leading to a safe, green and feasible way for the formation of C-3 diarylmethyl functionalized indole derivatives.

Original languageEnglish
Article numbere202200042
JournalChemistry - An Asian Journal
Volume17
Issue number9
DOIs
Publication statusPublished - 4 Mar 2022

Keywords

  • 1,6-hydroarylation
  • brønsted-acid catalysis
  • green media
  • indoles
  • para-quinone methides

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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