A facile synthesis of difluoromethylene compounds by oxidative fluorodesulfurization of dithioacetals using tetrabutylammonium dihydrogentrifluoride and N-halo compounds

Manabu Kuroboshi, Tamejiro Hiyama

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Cyclic dithioacetals of aldehydes and ketones are converted into the corresponding difluoromethylene compounds with characteristic chemoselectivity by means of tetrabutyl-ammonium dihydrogen trifluoride and N-halo amides or imides (N-bromosuccinimide, N-iodosuccinimide and l,3-dibromo-5,5-dimethylhydantoin) in good to excellent yield. The substrates which have an acid-sensitive functionality or other easily fluorinated functionalities give the desired products without any damage to that functionality.

Original languageEnglish
Pages (from-to)909-910
Number of pages2
JournalSynlett
Volume1991
Issue number12
DOIs
Publication statusPublished - Dec 1 1991
Externally publishedYes

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Bromosuccinimide
Imides
Ketones
Ammonium Compounds
Aldehydes
Amides
Acids
Substrates
tetrabutylammonium
5,5-dimethylhydantoin
N-iodosuccinimide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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T1 - A facile synthesis of difluoromethylene compounds by oxidative fluorodesulfurization of dithioacetals using tetrabutylammonium dihydrogentrifluoride and N-halo compounds

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AU - Hiyama, Tamejiro

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AB - Cyclic dithioacetals of aldehydes and ketones are converted into the corresponding difluoromethylene compounds with characteristic chemoselectivity by means of tetrabutyl-ammonium dihydrogen trifluoride and N-halo amides or imides (N-bromosuccinimide, N-iodosuccinimide and l,3-dibromo-5,5-dimethylhydantoin) in good to excellent yield. The substrates which have an acid-sensitive functionality or other easily fluorinated functionalities give the desired products without any damage to that functionality.

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