Pd-catalyzed cascade crossover annulation of o-alkynylarylhalides and diarylacetylenes leading to dibenzo[a,e]pentalenes

Jian Zhao, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto, Tienan Jin

Research output: Contribution to journalArticle

72 Citations (Scopus)

Abstract

A novel and selective Pd-catalyzed cascade crossover-annulation of o-alkynylarylhalides and diarylacetylenes for the synthesis of dibenzo[a,e]pentalenes has been reported. Various arylacetylenes with a wide range of functional groups were tolerated, producing the corresponding multisubstituted dibenzopentalenes with the different substituents on the aromatic rings in good to high yields under the optimized reaction conditions. The reaction proceeds through a Pd-catalyzed cascade carbopalladation and C-H activation. The use of the combined DBU and CsOPiv bases is crucial for the successful implementation of the present cross-annulation.

Original languageEnglish
Pages (from-to)10222-10225
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number28
DOIs
Publication statusPublished - 2013 Jul 17

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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