Palladium-catalyzed C-H benzannulation of functionalized furans and pyrroles with alkynes

Jia Seo, Che Wei Chen, Woohyeong Lee, Ju Eun Jeon, Pei Ling Chen, Shih Ching Chuang*, Jung Min Joo

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


A benzannulation strategy involving activation of two C-H bonds of five-membered heteroarenes was developed. Readily available furans and pyrroles stabilized by synthetically useful electron-withdrawing groups underwent Pd-catalyzed 1:2 annulation reactions with diaryl alkynes. A variety of functional groups, including ester, amide, ketone, aldehyde, and nitrile, on the heterocyclic cores were tolerated in the Pd-catalyzed oxidative reactions. In these reactions, the combination of 2,2-dimethylbutyric acid and its conjugate base facilitated metalation at the heteroaromatic rings and reoxidation of the Pd(0) species using oxygen as the terminal oxidant. This strategy provides fluorescent benzofuran and indole derivatives and is expected to allow for further development of functionalized polycyclic heteroaromatic compounds.

Original languageEnglish
Pages (from-to)3001-3010
Number of pages10
JournalSynthesis (Germany)
Issue number17
StatePublished - Sep 2021


  • Alkynes
  • Benzannulation
  • Furans
  • Indoles
  • Oxygen
  • Palladium
  • Pyrroles


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