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

Satoshi Ueno, Masakazu Ohtsubo, Ryoichi Kuwano

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

(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
Volume131
Issue number36
DOIs
Publication statusPublished - Sep 16 2009

Fingerprint

Imines
Cycloaddition
Cycloaddition Reaction
Palladium
Tetrahydroisoquinolines
Catalysts
Carbonates
Fluorides
Reaction rates
Substrates

All Science Journal Classification (ASJC) codes

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

Cite this

[4+2] Cycloaddition of o-xylylenes with imines using palladium catalyst. / Ueno, Satoshi; Ohtsubo, Masakazu; Kuwano, Ryoichi.

In: Journal of the American Chemical Society, Vol. 131, No. 36, 16.09.2009, p. 12904-12905.

Research output: Contribution to journalArticle

Ueno, Satoshi ; Ohtsubo, Masakazu ; Kuwano, Ryoichi. / [4+2] Cycloaddition of o-xylylenes with imines using palladium catalyst. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 36. pp. 12904-12905.
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