Brønsted Acid-Promoted Benzannulation of o-Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol

Cheng Chun Chen, Tzu Hsuan Kuan, Wen Wei Yuan, Shih En Chen, Jui Chen Fu, Yang Xun Chen, Hui Hsu Gavin Tsai, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Bromotrimethylsilane-promoted benzannulation of o-alkynylbenzaldehydes and alkynes to yield 1-naphthyl aryl ketones is reported. The reaction conditions are mild, metal-free, and do not require pretreatment/protection of the substrates. We found that aryl propargyl alcohols were very effective substrates for this reaction, compared with other alkynes. Studies on the reaction scope, monitoring the reaction progress by 1H NMR, and theoretical calculations suggest that isochromenylium (benzopyrilium) ion is the key reaction intermediate. (Figure presented.).

Original languageEnglish
Pages (from-to)4122-4134
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume364
Issue number23
DOIs
StatePublished - 8 Dec 2022

Keywords

  • benzannulation
  • isochromenylium
  • naphthalene
  • propargyl alcohol

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