Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds

Abstract

1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br₂ or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.

Original language	English
Pages (from-to)	3-16
Number of pages	14
Journal	Journal of Sulfur Chemistry
Volume	32
Issue number	1
DOIs	https://doi.org/10.1080/17415993.2010.537339 https://doi.org/10.1080/17415993.2010.537339
Publication status	Published - Feb 2011

Keywords

δ-sultones
alkynes
bromination
dioxane sulfotrioxide
Sonogashira coupling

ASJC Scopus subject areas

Chemistry(all)

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Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds. / Gaitzsch, Jens; Rogachev, Victor; Metz, Peter; Filimonov, Victor D.; Zahel, Martin; Kataeva, Olga.

In: Journal of Sulfur Chemistry, Vol. 32, No. 1, 02.2011, p. 3-16.

Research output: Contribution to journal › Article › peer-review

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abstract = "1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br2 or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.",

keywords = "δ-sultones, alkynes, bromination, dioxane sulfotrioxide, Sonogashira coupling",

author = "Jens Gaitzsch and Victor Rogachev and Peter Metz and Filimonov, {Victor D.} and Martin Zahel and Olga Kataeva",

year = "2011",

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AU - Filimonov, Victor D.

AU - Zahel, Martin

AU - Kataeva, Olga

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AB - 1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br2 or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.

KW - δ-sultones

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KW - bromination

KW - dioxane sulfotrioxide

KW - Sonogashira coupling

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