[4+2] Cycloaddition of o-xylylenes with imines using palladium catalyst

Satoshi Ueno, Masakazu Ohtsubo, Ryoichi Kuwano

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)


(Chemical Equation Presented) The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(η3- C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diels-Alder reaction of o-xylylene with imines.

Original languageEnglish
Pages (from-to)12904-12905
Number of pages2
JournalJournal of the American Chemical Society
Issue number36
Publication statusPublished - Sept 16 2009

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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