A facile synthesis of trifluoromethyl- and 3,3,3-trifluoropropenyl- substituted aromatic compounds by the oxidative desulfurization-fluorination of the corresponding carbodithioates

Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

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30 Citations (Scopus)

Abstract

Trifluoromethyl-substituted aromatic compounds were easily synthesized by the oxidative desulfurization-fluorination reaction of readily accessible methyl arenecarbodithioates using [n-Bu4N]H2F3 and 1,3-dibromo-5,5- dimethylhydantoin (DBH) under extremely mild conditions. Use of N- bromosuccinimide or N-iodosuccinimide instead of DBH afforded difluoro(methylthio)methyl-substituted aromatics. In a similar way, 3,3,3- trifluoropropenyl-substituted aromatic compounds were readily prepared from the corresponding α,β-unsaturated carbodithioates.

Original languageEnglish
Pages (from-to)805-819
Number of pages15
JournalBulletin of the Chemical Society of Japan
Volume72
Issue number4
DOIs
Publication statusPublished - Apr 1999

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Fluorination
Aromatic compounds
Desulfurization
Bromosuccinimide
N-iodosuccinimide
1,3-dibromo-5,5-dimethylhydantoin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Trifluoromethyl-substituted aromatic compounds were easily synthesized by the oxidative desulfurization-fluorination reaction of readily accessible methyl arenecarbodithioates using [n-Bu4N]H2F3 and 1,3-dibromo-5,5- dimethylhydantoin (DBH) under extremely mild conditions. Use of N- bromosuccinimide or N-iodosuccinimide instead of DBH afforded difluoro(methylthio)methyl-substituted aromatics. In a similar way, 3,3,3- trifluoropropenyl-substituted aromatic compounds were readily prepared from the corresponding α,β-unsaturated carbodithioates.",
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T1 - A facile synthesis of trifluoromethyl- and 3,3,3-trifluoropropenyl- substituted aromatic compounds by the oxidative desulfurization-fluorination of the corresponding carbodithioates

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AU - Kuroboshi, Manabu

AU - Hiyama, Tamejiro

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N2 - Trifluoromethyl-substituted aromatic compounds were easily synthesized by the oxidative desulfurization-fluorination reaction of readily accessible methyl arenecarbodithioates using [n-Bu4N]H2F3 and 1,3-dibromo-5,5- dimethylhydantoin (DBH) under extremely mild conditions. Use of N- bromosuccinimide or N-iodosuccinimide instead of DBH afforded difluoro(methylthio)methyl-substituted aromatics. In a similar way, 3,3,3- trifluoropropenyl-substituted aromatic compounds were readily prepared from the corresponding α,β-unsaturated carbodithioates.

AB - Trifluoromethyl-substituted aromatic compounds were easily synthesized by the oxidative desulfurization-fluorination reaction of readily accessible methyl arenecarbodithioates using [n-Bu4N]H2F3 and 1,3-dibromo-5,5- dimethylhydantoin (DBH) under extremely mild conditions. Use of N- bromosuccinimide or N-iodosuccinimide instead of DBH afforded difluoro(methylthio)methyl-substituted aromatics. In a similar way, 3,3,3- trifluoropropenyl-substituted aromatic compounds were readily prepared from the corresponding α,β-unsaturated carbodithioates.

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