A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithio carbonates

被引：60

作者：

Kanie, K ^{[1
]}

Tanaka, Y ^{[1
]}

Suzuki, K ^{[1
]}

Kuroboshi, M ^{[1
]}

Hiyama, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Resources Utilizat Res Lab, Midori Ku, Kanagawa 2268503, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2000年 / 73卷 / 02期

关键词：

D O I：

10.1246/bcsj.73.471

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Trifluoromethyl ethers R-OCF3 are easily synthesized from the corresponding dithiocarbonates R-OCS2Me (R = aryl or primary alkyl) by a reagent system consisting of 70% HF/pyridine and an N-halo imide. When the reaction is applied to R-OCS2Me wherein R = secondary alkyl, tertiary alkyl, or benzylic group, fluorination leading to the corresponding alkyl fluorides R-F is achieved, whereas a combination of 50% HF/pyridine and N-bromosuccinimide affords the corresponding trifluoromethyl ethers R-OCF3 (R = secondary).

引用

页码：471 / 484

页数：14

共 33 条

[1] Convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithiocarbonates
Kanie, Kiyoshi
Tanaka, Yoichiro
Suzuki, Kazundo
Kuroboshi, Manabu
Hiyama, Tamejiro
[J]. 1600, Chemical Soc of Japan, Tokyo, Japan (73):
[2] OXIDATIVE DESULFURIZATION-FLUORINATION OF XANTHATES - A CONVENIENT SYNTHESIS OF TRIFLUOROMETHYL ETHERS AND DIFLUORO(METHYLTHIO)METHYL ETHERS
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HIYAMA, T
[J]. TETRAHEDRON LETTERS, 1992, 33 (29) : 4173 - 4176
[3] A CONVENIENT SYNTHESIS OF PERFLUOROALKYLATED AMINES BY OXIDATIVE DESULFURIZATION-FLUORINATION
KUROBOSHI, M
HIYAMA, T
[J]. TETRAHEDRON LETTERS, 1994, 35 (23) : 3983 - 3984
[4] OXIDATIVE DESULFURIZATION-FLUORINATION OF METHYL ARENEDITHIOCARBOXYLATES - A CONVENIENT SYNTHESIS OF TRIFLUOROMETHYLATED AROMATIC-COMPOUNDS
KUROBOSHI, M
HIYAMA, T
[J]. CHEMISTRY LETTERS, 1992, (05) : 827 - 830
[5] Fluorination of orthothioesters through oxidative desulfurization-fluorination
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[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (08) : 1939 - 1951
[6] Oxidative desulfurization-fluorination reaction promoted by [bdmim][F] for the synthesis of difluminated methyl ethers
Bouvet, Sebastien
Pegot, Bruce
Diter, Patrick
Marrot, Jerome
Magnier, Emmanuel
[J]. TETRAHEDRON LETTERS, 2015, 56 (13) : 1682 - 1686
[7] A FACILE SYNTHESIS OF TRIFLUOROMETHYLAMINES BY OXIDATIVE DESULFURIZATION-FLUORINATION OF DITHIOCARBAMATES
KUROBOSHI, M
HIYAMA, T
[J]. TETRAHEDRON LETTERS, 1992, 33 (29) : 4177 - 4178
[8] A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamates
Kanie, K
Mizuno, K
Kuroboshi, M
Hiyama, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (08) : 1973 - 1991
[9] A FACILE SYNTHESIS OF ALPHA,ALPHA-DIFLUOROALKYL ETHERS AND CARBONYL FLUORIDE ACETALS BY OXIDATIVE DESULFURIZATION-FLUORINATION
KUROBOSHI, M
HIYAMA, T
[J]. SYNLETT, 1994, (04) : 251 - 252
[10] SYNTHESIS OF PERFLUOROALKYL-SUBSTITUTED ARENES BY OXIDATIVE DESULFURIZATION-FLUORINATION
KUROBOSHI, M
HIYAMA, T
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1994, 69 (02) : 127 - 128

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