Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/1,1-Carboxyalkynylation of Alkynylbenziodoxoles

Junliang Wu, Kai Xu, Hajime Hirao, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

A PdII-catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk-1-en-3-ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd-assisted 1,2-iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups (the latter originating from another molecule of the alkynylbenziodoxole) into the 1-position of the transient Pd-vinylidene species. The product of this 1,1-carboxyalkynylation reaction serves as a new functionalized enyne-type building block for further synthetic transformations.

Original languageEnglish
Pages (from-to)1521-1525
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number7
DOIs
Publication statusPublished - 2017 Jan 31
Externally publishedYes

Keywords

  • alkynylation
  • carboxylic acid
  • cross-coupling
  • hypervalent iodine
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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