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

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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 (US)
Pages (from-to)3335-3338
Number of pages4
JournalOrganic Letters
Volume9
Issue number17
DOIs
StatePublished - Aug 16 2007
Externally publishedYes

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