Palladium-catalyzed construction of poly-substituted indolizinones

Hanyang Cho, Ikyon Kim

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elimination, and 1,2-shift. While our previous effort to the same skeleton via 2-iodoindolizinones selected α,β-unsaturated esters, terminal acetylenes, or boronic acids as coupling partners, this strategy introduces new functional groups at the C2 position of indolizinone core with (hetero)aryl halides or diallyl carbonate, expanding the substrate scope for decoration at the C2 site. Furthermore, a new preparation route to tertiary propargylic alcohols for this study is described to rapidly diversify the molecular framework.

Original languageEnglish
Pages (from-to)5464-5480
Number of pages17
JournalTetrahedron
Volume68
Issue number27-28
DOIs
Publication statusPublished - 2012 Jul 8

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Palladium
Alcohols
Boronic Acids
Alkynes
Carbonates
Skeleton
Functional groups
Esters
Substrates

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Cho, Hanyang ; Kim, Ikyon. / Palladium-catalyzed construction of poly-substituted indolizinones. In: Tetrahedron. 2012 ; Vol. 68, No. 27-28. pp. 5464-5480.
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Palladium-catalyzed construction of poly-substituted indolizinones. / Cho, Hanyang; Kim, Ikyon.

In: Tetrahedron, Vol. 68, No. 27-28, 08.07.2012, p. 5464-5480.

Research output: Contribution to journalArticle

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