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

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 language	English
Pages (from-to)	3335-3338
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	17
DOIs	https://doi.org/10.1021/ol071345q
Publication status	Published - 16 Aug 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.

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title = "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",

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.",

author = "Masahito Ochiai and Masaya Hirobe and Akira Yoshimura and Yoshio Nishi and Kazunori Miyamot and Motoo Shiro",

year = "2007",

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doi = "10.1021/ol071345q",

language = "English",

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journal = "Organic Letters",

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T1 - Internal delivery of soft chlorine and bromine atoms

T2 - Stereoselective synthesis of (E)-β-halogenovinyl(aryl)-λ3-iodanes through domino λ3-lodanation-1,4-halogen shift-fluorination of alkynes

AU - Ochiai, Masahito

AU - Hirobe, Masaya

AU - Yoshimura, Akira

AU - Nishi, Yoshio

AU - Miyamot, Kazunori

AU - Shiro, Motoo

PY - 2007/8/16

Y1 - 2007/8/16

N2 - 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.

AB - 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.

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