Electrolytic partial fluorination of organic compounds. Part 48: Anodic fluorination of 2-cyano-1-methylpyrrole

Toshiki Tajima; Hideki Ishii; Toshio Fuchigami

doi:10.1016/S0040-4039(01)00866-8

Electrolytic partial fluorination of organic compounds. Part 48: Anodic fluorination of 2-cyano-1-methylpyrrole

Toshiki Tajima, Hideki Ishii, Toshio Fuchigami

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

19 Citations (Scopus)

Abstract

Anodic fluorination of 2-cyano-1-methylpyrrole using Et₃N·2HF in an undivided cell provided the corresponding 5-fluoropyrrole and 2,5,5-trifluoro-1-methyl-3-pyrrolin-2-carbonitrile while the use of Et₃N·3HF afforded selectively the latter product, which was readily hydrolyzed to isolable 5,5-difluoro-1-methyl-3-pyrroline-2-one. This is the first report of successful anodic fluorination of a pyrrole derivative.

Original language	English
Pages (from-to)	4857-4860
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4039(01)00866-8
Publication status	Published - 2001 Jul 16
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Electrolytic partial fluorination of organic compounds. Part 48: Anodic fluorination of 2-cyano-1-methylpyrrole",

abstract = "Anodic fluorination of 2-cyano-1-methylpyrrole using Et3N·2HF in an undivided cell provided the corresponding 5-fluoropyrrole and 2,5,5-trifluoro-1-methyl-3-pyrrolin-2-carbonitrile while the use of Et3N·3HF afforded selectively the latter product, which was readily hydrolyzed to isolable 5,5-difluoro-1-methyl-3-pyrroline-2-one. This is the first report of successful anodic fluorination of a pyrrole derivative.",

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AU - Ishii, Hideki

AU - Fuchigami, Toshio

PY - 2001/7/16

Y1 - 2001/7/16

N2 - Anodic fluorination of 2-cyano-1-methylpyrrole using Et3N·2HF in an undivided cell provided the corresponding 5-fluoropyrrole and 2,5,5-trifluoro-1-methyl-3-pyrrolin-2-carbonitrile while the use of Et3N·3HF afforded selectively the latter product, which was readily hydrolyzed to isolable 5,5-difluoro-1-methyl-3-pyrroline-2-one. This is the first report of successful anodic fluorination of a pyrrole derivative.

AB - Anodic fluorination of 2-cyano-1-methylpyrrole using Et3N·2HF in an undivided cell provided the corresponding 5-fluoropyrrole and 2,5,5-trifluoro-1-methyl-3-pyrrolin-2-carbonitrile while the use of Et3N·3HF afforded selectively the latter product, which was readily hydrolyzed to isolable 5,5-difluoro-1-methyl-3-pyrroline-2-one. This is the first report of successful anodic fluorination of a pyrrole derivative.

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Electrolytic partial fluorination of organic compounds. Part 48: Anodic fluorination of 2-cyano-1-methylpyrrole

Abstract

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