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Arylbis (perfluoroalkylsulfonyl) methane, metal salf of same, and processes for producing these

A perfluoroalkyl sulfonyl and perfluoroalkyl sulfinate technology, which is applied to the preparation of carbon-based compounds, carboxylate esters, chemical instruments and methods, etc., can solve the problem of unsuitable raw materials and difficult molecular New functions, not easy to chemically modify, etc.

Inactive Publication Date: 2004-03-10
JAPAN SCI & TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Organic acids with trifluoromethanesulfonyl groups in the past, known as TfOH, Tf 2 NH, Tf 2 CH 2 、Tf 3 CH, but these molecules are not easy to chemically modify, and it is difficult to make molecules with new functions
Therefore, it is not suitable for use as raw materials for the preparation of medicines, pesticides, asymmetric catalysts, and various functional materials.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Infrared spectra were measured with Shimadzu's FTIR-9100. 1 H NMR spectrum was measured with a VarianGemini-300 (300MHz) nuclear magnetic resonance device. 1 H NMR chemical shifts are expressed in ppm of the solvent used as internal standard (0 ppm tetramethylsilane). Splitting patterns use s, d, t, q, m, and br to denote singlet, doublet, triplet, quartet, multiplet, and broad, respectively. 13 The C NMR spectrum was measured with a Varian Gemini-300 (125MHz) nuclear magnetic resonance device, used as an internal standard (77.0ppm of CDCl 3 ) expressed in ppm of solvent used. 19 The FNMR spectrum was measured with a Varian Gemini-300 (282MHz) nuclear magnetic resonance device, used as an internal standard (-64.0ppm CF 3 C 6 h 5 ) expressed in ppm of solvent used. High performance liquid chromatography (HPLC) analysis was performed using a Shimadzu LC-10AD instrument and SPD-M10A UV detector with a chiral column (Daicel AS or OD-H). The following examples are all...

Embodiment 2

[0101] Infrared spectra were measured with Shimadzu's FTIR-9100. 1 H NMR spectrum was measured with a VarianGemini-300 (300MHz) nuclear magnetic resonance device. 1 H NMR chemical shifts are expressed in ppm of the solvent used as internal standard (0 ppm tetramethylsilane). Splitting patterns use s, d, t, q, m, and br to denote singlet, doublet, triplet, quartet, multiplet, and broad, respectively. 13 The C NMR spectrum was measured with a Varian Gemini-300 (125MHz) nuclear magnetic resonance device, used as an internal standard (77.0ppm of CDCl 3 ) expressed in ppm of solvent used. 19 The FNMR spectrum was measured with a Varian Gemini-300 (282MHz) nuclear magnetic resonance device, used as an internal standard (-64.0ppm CF 3 C 6 h 5 ) expressed in ppm of solvent used. High performance liquid chromatography (HPLC) analysis was performed using a Shimadzu LC-10AD instrument and SPD-M10A UV detector with a chiral column (Daicel AS or OD-H). The following examples are all...

Embodiment 3

[0119] Pentafluorophenylmethyl Triflone: ​​IR (KBr) 1509, 1374, 1210, 1121, 995cm -1 ; 1 H NMR (CDCl 3 , 300MHz) δ4.64; 13 C NMR (CDCl 3 , 125MHz) δ44.3, 100.0 (dt, J CF =4, 17Hz, 1C, ipso-C), 119.5(q, J CF =326Hz, 1C, CF 3 ), 137.9 (d, J CF =251Hz, 2C, 2m-C), 142.8(d, J CF =258Hz, 1C, p-C), 145.9(d, J CF = 252Hz, 2C, 2o-C); 19 F NMR (CDCl 3, 282MHz) δ-160.0(d, J=15.2Hz, 2F, 2m-F), 149.0(s, 1F, p-F), 139.4(d, J=15.2Hz, 2F, 2o-F), -78.3(s , 3F, CF 3 ).Anal.Calcd for C 8 h 2 o 2 f 8 S: C, 30.59; H, 0.64; F, 48.38; S, 10.21.Found C, 30.49; H, 0.73; F, 48.37; S, 10.18. Synthetic research)

[0120] The benzyltrifluoromethyl sulfone (0.5 mmol) obtained in Example 2 was dissolved in ether (3 milliliters), and after the solution was cooled to -78° C., 2.2 equivalents (1.1 mmol) of tert-butyllithium ( 0.34 ml, 1.6M solution in pentane), stirred for 0.5 hours. Then add Tf 2 O (46 μL, 0.55 mmol), the temperature of the reaction solution was raised to room temperature ...

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PUM

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Abstract

The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmertric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfonic acid anhydride, and an arylbis(trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.

Description

technical field [0001] The invention relates to a method for preparing aryl bis(perfluoroalkylsulfonyl)methane such as aryl bis(trifluoromethanesulfonyl)methane by using sodium trifluoromethanesulfinate and trifluoromethanesulfonic anhydride, and using this preparation Pentafluorophenylbis(trifluoromethanesulfonyl)methane and {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(trifluoromethanesulfonyl)methane, etc. New arylbis(perfluoroalkylsulfonyl)methanes as electrophilic reactants for trifluoromethanesulfonyl sources. [0002] And the present invention also relates to metal salts of arylbis(perfluoroalkylsulfonyl)methane, i.e. metal arylbis(perfluoroalkylsulfonyl)methane and the preparation method of this compound, and using this compound as an effective Components of catalysts such as Lewis acid catalysts and synthesis methods of organic compounds using such catalysts. Background technique [0003] Known trifluoromethanesulfonyl (-SO 2 CF 3 ; Trifluoromethanesulfon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02B01J31/12C07C45/69C07C67/08C07C317/10
CPCC07C45/69B01J2231/40B01J2231/49C07C67/08B01J2231/326B01J31/0227B01J2231/122C07C317/10B01J31/122C07C47/445C07C69/78
Inventor 石原一彰山本尚
Owner JAPAN SCI & TECH CORP
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