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 journal › Article

30 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

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Bromine
Fluorination
Stereochemistry
Halogens
fluorination
Alkynes
Halogenation
Chlorine
Toluene
alkynes
bromine
halogens
chlorine
delivery
Ions
Atoms
rings
shift
stereochemistry
synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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

In: Organic Letters, Vol. 9, No. 17, 16.08.2007, p. 3335-3338.

Research output: Contribution to journal › Article

Ochiai, M, Hirobe, M, Yoshimura, A, Nishi, Y, Miyamot, K & Shiro, M 2007, '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', Organic Letters, vol. 9, no. 17, pp. 3335-3338. https://doi.org/10.1021/ol071345q
Ochiai M, Hirobe M, Yoshimura A, Nishi Y, Miyamot K, Shiro M. 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. Organic Letters. 2007 Aug 16;9(17):3335-3338. https://doi.org/10.1021/ol071345q
Ochiai, Masahito ; Hirobe, Masaya ; Yoshimura, Akira ; Nishi, Yoshio ; Miyamot, Kazunori ; Shiro, Motoo. / 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. In: Organic Letters. 2007 ; Vol. 9, No. 17. pp. 3335-3338.
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