A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates

Kiyoshi Kanie; Katsuya Mizuno; Manabu Kuroboshi; Tamejiro Hiyama

doi:10.1246/bcsj.71.1973

A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates

Kiyoshi Kanie, Katsuya Mizuno, Manabu Kuroboshi, Tamejiro Hiyama

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

59 Citations (Scopus)

Abstract

Trifluoromethylamines are easily synthesized from dithiocarbamates by a reagent system consisting of tetrabutylammonium dihydrogentrifluoride and an N-halo imide under mild conditions. When this reaction was applied to dithiocarbamates ArN(R)CS₂Me at higher temperatures, the trifluoromethylation was accompanied by halogen substitution at the p-position of the Ar group. The synthesis of trifluoromethyl-substituted adenosine is also described.

Original language	English
Pages (from-to)	1973-1991
Number of pages	19
Journal	Bulletin of the Chemical Society of Japan
Volume	71
Issue number	8
DOIs	https://doi.org/10.1246/bcsj.71.1973
Publication status	Published - 1998 Aug
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1246/bcsj.71.1973

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author = "Kiyoshi Kanie and Katsuya Mizuno and Manabu Kuroboshi and Tamejiro Hiyama",

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AU - Hiyama, Tamejiro

PY - 1998/8

Y1 - 1998/8

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AB - Trifluoromethylamines are easily synthesized from dithiocarbamates by a reagent system consisting of tetrabutylammonium dihydrogentrifluoride and an N-halo imide under mild conditions. When this reaction was applied to dithiocarbamates ArN(R)CS2Me at higher temperatures, the trifluoromethylation was accompanied by halogen substitution at the p-position of the Ar group. The synthesis of trifluoromethyl-substituted adenosine is also described.

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A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates

Abstract

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