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

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

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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, 9(17), 3335-3338. https://doi.org/10.1021/ol071345q

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

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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.",

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AU - Ochiai, Masahito

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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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10.1021/ol071345q