Internal delivery of soft chlorine and bromine atoms: Stereoselective synthesis of (E)-β-halogenovinyl(aryl)-λ3-iodanes through domino λ3-lodanation-1,4-halogen shift-fluorination of alkynes

Masahito Ochiai, Masaya Hirobe, Akira Yoshimura, Yoshio Nishi, Kazunori Miyamot, Motoo Shiro

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

X = Cl, Br; n = 1-3 4-(Difluoroiodo)toluene-induced domino λ3-iodanation-1,4-halogen shift-ring enlargement-fluorination reaction of 5-halopentynes with a four-, five-, or six-membered carbocycle afforded the ring-expanded (E)-δ-fluoro-β-halovinyl- λ3-iodanes stereoselectively in high yields, probably via the intermediacy of five-membered halonium ions. Use of internal alkynes makes it possible to synthesize tetrasubstltuted β-halovinyl-λ3- iodanes with defined stereochemistry.

Original languageEnglish
Pages (from-to)3335-3338
Number of pages4
JournalOrganic Letters
Volume9
Issue number17
DOIs
Publication statusPublished - 16 Aug 2007
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Internal delivery of soft chlorine and bromine atoms: Stereoselective synthesis of (E)-β-halogenovinyl(aryl)-λ<sup>3</sup>-iodanes through domino λ<sup>3</sup>-lodanation-1,4-halogen shift-fluorination of alkynes'. Together they form a unique fingerprint.

  • Cite this