Development of π-acidic metal-catalyzed reactions toward construction of multi-substituted heterocycles

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Abstract

π-Acidic metal-catalyzed cyclization reaction is one of the most efficient methods to construct highly elaborate molecular skeletons in a single operation under mild reaction conditions. These transformations often involve cleavage of σ bonds. Investigations into catalytic skeletal rearrangement have mainly utilized alkynylamines, alkynylalcohols, enynes, and propargylic esters as substrates. In this article, I report our recent findings on π-acidic metal catalyzed reactions via cleavage of σ bonds between major elements in body, such as carbon, nitrogen, oxygen, and sulfur, producing multisubstituted heterocycles in an atom efficient manner. That is, (a) catalytic carbon-heteroatom bond addition of ortho-alkynylphenyl ethers, -anilines, and -phenyl sulildes and (b) catalytic skeletal rearrangement of propargylic oximes.

Original languageEnglish
Pages (from-to)581-592
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume70
Issue number6
DOIs
Publication statusPublished - 2012 Dec 1

Keywords

  • 1-3 migration
  • Alkyne activation
  • Copper catalyst
  • Gold catalyst
  • Heteroarenes
  • Metal carbenoid
  • Oxime
  • Platinum catalyst
  • Skeletal rearrangement
  • [2.3] rearrangement

ASJC Scopus subject areas

  • Organic Chemistry

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