Palladium(0)-catalyzed cis-selective alkylative and arylative cyclization of alkynyl enones with organoboron reagents

Hirokazu Tsukamoto, Takamichi Suzuki, Tomomi Uchiyama, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

A palladium(0)-tricyclohexylphosphine catalyzes cis-selective alkylative and arylative cyclization of alkyne-containing electron-deficient alkenes with organoboron reagents to provide five- or six-membered rings with exo tri- or tetra-substituted alkenes. The opposite stereoselectivity to that for the alkyne-aldehyde cyclization using the same reagents would result from palladacycle-forming oxidative addition of the substrates to the Pd0 catalyst followed by transmetalation with the boron reagents, protonation, and reductive elimination. The functional group compatibility, availability, stability, and non-toxicity of the reagents, and the fact that no additives are needed make the process more practical than the Ni0-catalyzed cyclization with organozinc reagents.

Original languageEnglish
Pages (from-to)4174-4177
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number26
DOIs
Publication statusPublished - 2008 Jun 23

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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