Palladium(0)-catalyzed alkylative cyclization of alkynals and alkynones: Remarkable trans-addition of organoboronic reagents

Hirokazu Tsukamoto, Tatsuhiko Ueno, Yoshinori Kondo

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

Palladium/monophosphine complexes catalyze trans-selective arylative, alkenylative, and alkylative cyclization reactions of alkynals and alkynones with organoboronic reagents. These reactions afford six-membered allylic alcohols with endo-tri- or tetrasubstituted olefin groups and/or five-membered counterparts with exo olefin groups. The ratios of these products are dramatically affected by alkyne substituents as well as the phosphine ligand. The remarkable trans-selectivity of the process results from the novel reaction mechanism involving oxidative addition without oxametallacycle formation.

Original languageEnglish
Pages (from-to)1406-1407
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number5
DOIs
Publication statusPublished - 2006 Feb 8

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Palladium(0)-catalyzed alkylative cyclization of alkynals and alkynones: Remarkable trans-addition of organoboronic reagents'. Together they form a unique fingerprint.

  • Cite this