Pd-Catalyzed Conversion of Alkynyl-λ3-iodanes to Alkenyl-λ3-iodanes via Stereoselective 1,2-Iodine(III) Shift/1,1-Hydrocarboxylation

Junliang Wu, Xiaozhou Deng, Hajime Hirao, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

Alkynyl-λ3-iodanes have been established as alkynyl cation equivalents for the alkynylation of carbon- and heteroatom-based nucleophiles. Herein, we report an unprecedented reaction mode of this compound class, which features a Pd(II)-assisted 1,2-I(III) shift of an alkynylbenziodoxole. A Pd(II) catalyst mediates this shift and the subsequent interception of the transient vinylidene species with carboxylic acid (1,1-hydrocarboxylation). The product of this stereoselective rearrangement-addition reaction, β-oxyalkenylbenziodoxole, represents a novel and useful building block for further synthetic transformations.

Original languageEnglish
Pages (from-to)9105-9108
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number29
DOIs
Publication statusPublished - 2016 Jul 27
Externally publishedYes

ASJC Scopus subject areas

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

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