Electrolytic partial fluorination of organic compounds. Part 78: Regioselective anodic fluorination of 2-oxazolidinones

Yi Cao; Katsutoshi Suzuki; Toshiki Tajima; Toshio Fuchigami

doi:10.1016/j.tet.2005.04.057

Electrolytic partial fluorination of organic compounds. Part 78: Regioselective anodic fluorination of 2-oxazolidinones

Yi Cao, Katsutoshi Suzuki, Toshiki Tajima, Toshio Fuchigami

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

12 Citations (Scopus)

Abstract

Various 2-oxazolidinones were galvanostatically electrooxidized in the presence of various fluoride salts. It was found that a fluorine atom was introduced to the α-position of the nitrogen atom of N-acyl- and N-alkoxycarbonyl-2-oxazolidinones to provide the corresponding α-fluorinated products in moderate to good yields. In the case of N-phenoxycarbonyl derivative, fluorination took place on the phenyl group selectively.

Original language	English
Pages (from-to)	6854-6859
Number of pages	6
Journal	Tetrahedron
Volume	61
Issue number	28
DOIs	https://doi.org/10.1016/j.tet.2005.04.057
Publication status	Published - 2005 Jul 11
Externally published	Yes

Keywords

2-Oxazolidinone
Electrochemical fluorination
Fluorinated 2-oxazolidinone
Partial fluorination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Electrolytic partial fluorination of organic compounds. Part 78: Regioselective anodic fluorination of 2-oxazolidinones",

abstract = "Various 2-oxazolidinones were galvanostatically electrooxidized in the presence of various fluoride salts. It was found that a fluorine atom was introduced to the α-position of the nitrogen atom of N-acyl- and N-alkoxycarbonyl-2-oxazolidinones to provide the corresponding α-fluorinated products in moderate to good yields. In the case of N-phenoxycarbonyl derivative, fluorination took place on the phenyl group selectively.",

keywords = "2-Oxazolidinone, Electrochemical fluorination, Fluorinated 2-oxazolidinone, Partial fluorination",

author = "Yi Cao and Katsutoshi Suzuki and Toshiki Tajima and Toshio Fuchigami",

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doi = "10.1016/j.tet.2005.04.057",

language = "English",

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T1 - Electrolytic partial fluorination of organic compounds. Part 78

T2 - Regioselective anodic fluorination of 2-oxazolidinones

AU - Cao, Yi

AU - Suzuki, Katsutoshi

AU - Tajima, Toshiki

AU - Fuchigami, Toshio

PY - 2005/7/11

Y1 - 2005/7/11

N2 - Various 2-oxazolidinones were galvanostatically electrooxidized in the presence of various fluoride salts. It was found that a fluorine atom was introduced to the α-position of the nitrogen atom of N-acyl- and N-alkoxycarbonyl-2-oxazolidinones to provide the corresponding α-fluorinated products in moderate to good yields. In the case of N-phenoxycarbonyl derivative, fluorination took place on the phenyl group selectively.

AB - Various 2-oxazolidinones were galvanostatically electrooxidized in the presence of various fluoride salts. It was found that a fluorine atom was introduced to the α-position of the nitrogen atom of N-acyl- and N-alkoxycarbonyl-2-oxazolidinones to provide the corresponding α-fluorinated products in moderate to good yields. In the case of N-phenoxycarbonyl derivative, fluorination took place on the phenyl group selectively.

KW - 2-Oxazolidinone

KW - Electrochemical fluorination

KW - Fluorinated 2-oxazolidinone

KW - Partial fluorination

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DO - 10.1016/j.tet.2005.04.057

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JF - Tetrahedron

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