CN105481738A - Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper - Google Patents
Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper Download PDFInfo
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- CN105481738A CN105481738A CN201610048828.3A CN201610048828A CN105481738A CN 105481738 A CN105481738 A CN 105481738A CN 201610048828 A CN201610048828 A CN 201610048828A CN 105481738 A CN105481738 A CN 105481738A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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Abstract
The invention discloses a method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper. The method includes the steps that copper iodide is adopted as a catalyst, diimine is adopted as a bidentate ligand, arene halogen, powdered sulfur and 2,2,2-trifluoro-ethyl iodide are adopted as reactants, sodium borohydride is adopted as a reducing agent, stirring is conducted for 1-24 hours at the temperature of 80 DEG C to 95 DEG C in an N,N-dimethyl formamide solvent, aftertreatment is conducted on reaction liquid after the reaction is completed, and the arene 2,2,2-trifluoro-ethyl sulfide compound is obtained. The synthesis method has the advantages that the catalyst is low in price, easy to obtain and low in toxicity, the raw materials are easy to obtain, operation is easy and convenient, and the universality of functional groups is good.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to a kind of method that copper catalyzes and synthesizes aromatic hydrocarbons 2,2,2-trifluoroethyl thioether.
Background technology
Fluoro-containing group has electron-withdrawing and height parent ester by force, shows many very unique physical propertiess and chemical property.Introduce fluoro-containing group in molecule after, significantly can change the polarity of molecule, reduce PKa value and improve membrane permeability, also have impact on pathways metabolism and the Pharmacokinetic Characteristics of molecule simultaneously.In numerous fluoro-containing group compound, receive concern especially containing 2,2,2-trifluoro ethylmercapto group compound, have in bioactive molecules containing this group many.But, up to the present, synthesize the few of the method report of aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, mainly reacted by aromatic hydrocarbons thiophenol and 2,2,2-trifluoroethyl haloalkane and obtain.But due to aromatic hydrocarbons thiophenol be not easy to obtain, expensive, and there is strong stink, therefore invent a kind of method utilizing that some are easy to get, cheap Material synthesis aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, there is important using value.
Summary of the invention
The object of the present invention is to provide a kind of copper to catalyze and synthesize the method for aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, this method cheaper starting materials is easy to get, and productive rate is high, and the adaptability of functional group is fine, and its operation is easy, has good prospects for commercial application.
For achieving the above object, the present invention adopts following technical scheme:
A kind of copper catalyzes and synthesizes the method for aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, take cuprous iodide as catalyzer, diimine is bitooth ligand, aromatic hydrocarbons halogen, sulphur powder and 2,2,2-trifluoro iodoethane is reactant, and sodium borohydride is reductive agent, at N, the obtained aromatic hydrocarbons 2 of reaction in dinethylformamide solvent, 2,2-trifluoroethyl thioether, chemical equation is:
。
The structural formula of described aromatic hydrocarbons halogen is:
, X is Br or I, and the structural formula of described aromatic hydrocarbons 2,2,2-trifluoroethyl thioether is:
, R is any one in following formula 1-formula 39:
The structural formula of described diimine is:
, wherein, R
1and R
2independently be selected from H or alkyl.
The mol ratio of described cuprous iodide, diimine part, aromatic hydrocarbons halogen, sulphur powder, 2,2,2-trifluoro iodoethane and sodium borohydride is 0.1-1:0.1-1:1:1-3:1-3:2-4.
Preferably, the mol ratio of described cuprous iodide, diimine part, aromatic hydrocarbons halogen, sulphur powder, 2,2,2-trifluoro iodoethane and sodium borohydride is 0.1:0.2:1:2:2:3.
The preparation method of described aromatic hydrocarbons 2,2,2-trifluoroethyl thioether specifically comprises the following steps:
To with add in the container of magnetic stirring apparatus cuprous iodide, diimine part, aromatic hydrocarbons halogen, sulphur powder, 2,2,2-trifluoro iodoethane, sodium borohydride and DMF, stopper is shut after mixing, put it in 80-95 DEG C of oil bath and continue to stir 1-24 hour, by extracted with diethyl ether, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filters, and then revolves and steams removing organic solvent; The crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains aromatic hydrocarbons 2,2,2-trifluoroethyl thioether.
Beneficial effect of the present invention is:
The present invention is with industrial aromatic hydrocarbons halogen cheap and easy to get, sulphur powder, 2,2,2-trifluoro iodoethane etc. is raw material, take cuprous iodide as catalyzer synthesis aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, obtain general higher productive rate, the adaptability of functional group is fine, and its operation is easy, has good prospects for commercial application.
Embodiment
More being convenient to make content of the present invention understand, below in conjunction with embodiment, technical solutions according to the invention are described further, but the present invention being not limited only to this.
Embodiment 1
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol2-iodo-benzoic acid methyl esters, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 80 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 2-(2,2,2-trifluoro ethylmercapto group) methyl benzoate (isolated yield 83%).
1HNMR(400MHz,CDCl
3)δ7.96(d,J=8.6Hz,1H),7.59–7.42(m,2H),7.36–7.29(m,1H),3.96(s,3H),3.60(q,J=9.7Hz,2H).
19FNMR(376MHz,CDCl
3)δ-65.2(t,J=9.7Hz,3F)。GC-MSm/z250(M
+)。
Embodiment 2
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol2-cyano group iodobenzene, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 80 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 2-(2,2,2-trifluoro ethylmercapto group) cyanobenzene (isolated yield 76%).
1HNMR(400MHz,CDCl
3)δ7.77–7.65(m,2H),7.60(t,J=7.7Hz,1H),7.45(t,J=7.8Hz,1H),3.58(q,J=9.5Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.1(t,J=9.4Hz,3F)。GC-MSm/z217(M
+)。
Embodiment 3
In nitrogen atmosphere, in a reactor, put into tetrafluoroethylene magnetite one, then add 0.050mmol cuprous iodide, 0.10mmol1,10-phenanthroline, 0.50mmol1-iodine naphthalene, 1.0mmol sulphur powder, 1.0mmol2,2,2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 85 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merges organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filters, and then revolves and steams removing organic solvent; The crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 1-(2,2,2-trifluoroethyl) naphthalene thioether (isolated yield 92%).
1HNMR(400MHz,CDCl
3)δ8.52(d,J=8.5Hz,1H),7.91(m,3H),7.63(m,2H),7.48(t,J=7.7Hz,1H),3.49(q,J=9.7Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.0(t,J=9.8Hz,3F)。GC-MSm/z242(M
+)。
Embodiment 4
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-iodanisol, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 85 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoro ethylmercapto group) methyl-phenoxide (isolated yield 84%).
1HNMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,2H),6.89(d,J=8.8Hz,2H),3.83(s,3H),3.34(q,J=9.8Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.3(t,J=9.8Hz,3F)。GC-MSm/z222(M
+)。
Embodiment 5
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-tertiary butyl iodobenzene, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 90 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoroethyl) tert.-butylbenzene thioether (isolated yield 66%).
1HNMR(400MHz,CDCl
3)δ7.49(d,J=7.1Hz,2H),7.41(d,J=7.2Hz,2H),3.46(q,J=9.7Hz,2H),1.37(d,J=1.4Hz,9H).
19FNMR(376MHz,CDCl
3)δ-66.3(t,J=9.7Hz,3F)。GC-MSm/z248(M
+)。
Embodiment 6
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-nitro iodobenzene, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 80 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoroethyl) oil of mirbane thioether (isolated yield 99%).
1HNMR(400MHz,CDCl
3)δ8.20(d,J=8.9Hz,2H),7.54(d,J=8.9Hz,2H),3.63(q,J=9.4Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.1(t,J=9.4Hz,3F)。GC-MSm/z236(M
+)。
Embodiment 7
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol3-nitro iodobenzene, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 85 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 3-(2,2,2-trifluoroethyl) oil of mirbane thioether (isolated yield 87%).
1HNMR(400MHz,CDCl
3)δ8.35(s,1H),8.18(dd,J=8.2,2.1Hz,1H),7.81(d,J=7.8Hz,1H),7.55(t,J=8.0Hz,1H),3.56(q,J=9.4Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.2(t,J=9.4Hz,3F)。GC-MSm/z236(M
+)。
Embodiment 8
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-cyano group iodobenzene, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 80 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoroethyl) cyano group diphenyl sulfide (isolated yield 93%).
1HNMR(400MHz,CDCl
3)δ7.62(d,J=8.5Hz,2H),7.50(d,J=8.5Hz,2H),3.57(q,J=9.4Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.1(t,J=9.4Hz,3F)。GC-MSm/z216(M
+)。
Embodiment 9
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-chloroiodobenzone, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 80 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoro ethylmercapto group) chlorobenzene (isolated yield 90%).
1HNMR(400MHz,CDCl
3)δ7.46(d,J=8.5Hz,2H),7.33(d,J=8.5Hz,2H),3.43(q,J=9.6Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.3(t,J=9.6Hz,3F)。GC-MSm/z226(M
+)。
Embodiment 10
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-methyl iodobenzene, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 90 DEG C of stirring reaction 16h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoro ethylmercapto group) toluene (isolated yield 83%).
1HNMR(400MHz,CDCl
3)δ7.43(d,J=8.1Hz,2H),7.17(d,J=7.9Hz,2H),3.42(q,J=9.8Hz,2H),2.38(s,3H).
19FNMR(376MHz,CDCl
3)δ-66.4(t,J=9.8Hz,3F)。GC-MSm/z205(M
+)。
Embodiment 11
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-bromo nitrobenzene, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 95 DEG C of stirring reaction 1h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoro ethylmercapto group) oil of mirbane (isolated yield 99%).
1HNMR(400MHz,CDCl
3)δ8.20(d,J=8.9Hz,2H),7.54(d,J=8.9Hz,2H),3.63(q,J=9.4Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.1(t,J=9.4Hz,3F)。GC-MSm/z236(M
+)。
Embodiment 12
In nitrogen atmosphere, tetrafluoroethylene magnetite one is put in a reactor, add 0.050mmol cuprous iodide again, 0.10mmol1, 10-phenanthroline, 0.50mmol4-bromoanisole, 1.0mmol sulphur powder, 1.0mmol2, 2, 2-trifluoro iodoethane, 1.5mmol sodium borohydride, finally add 5mLN, dinethylformamide, in enclosed system after 95 DEG C of stirring reaction 24h, be cooled to room temperature, by extracted with diethyl ether 3 times, each 10mL, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent, the crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains 4-(2,2,2-trifluoro ethylmercapto group) methyl-phenoxide (isolated yield 81%).
1HNMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,2H),6.89(d,J=8.8Hz,2H),3.83(s,3H),3.34(q,J=9.8Hz,2H).
19FNMR(376MHz,CDCl
3)δ-66.3(t,J=9.8Hz,3F)。GC-MSm/z222(M
+)。
The foregoing is only preferred embodiment of the present invention, all equalizations done according to the present patent application the scope of the claims change and modify, and all should belong to covering scope of the present invention.
Claims (6)
1. a copper catalyzes and synthesizes the method for aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, it is characterized in that: take cuprous iodide as catalyzer, diimine is bitooth ligand, aromatic hydrocarbons halogen, sulphur powder and 2,2,2-trifluoro iodoethane is reactant, is reductive agent, at N with sodium borohydride, the obtained aromatic hydrocarbons 2 of reaction in dinethylformamide solvent, 2,2-trifluoroethyl thioether, the structural formula of described aromatic hydrocarbons halogen is:
, X is Br or I.
2. a kind of copper according to claim 1 catalyzes and synthesizes the method for aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, it is characterized in that: the R in aromatic hydrocarbons halogen structural formula is any one in following formula 1-formula 39:
。
3. a kind of copper according to claim 1 catalyzes and synthesizes the method for aromatic hydrocarbons 2,2,2-trifluoroethyl thioether, it is characterized in that: the structural formula of described diimine is:
, wherein, R
1and R
2independently be selected from H or alkyl.
4. a kind of copper according to claim 1 catalyzes and synthesizes aromatic hydrocarbons 2, the method of 2,2-trifluoroethyl thioether, is characterized in that: cuprous iodide, diimine, aromatic hydrocarbons halogen, sulphur powder, 2, the mol ratio of 2,2-trifluoro iodoethane and sodium borohydride is 0.1-1:0.1-1:1:1-3:1-3:2-4.
5. a kind of copper according to claim 4 catalyzes and synthesizes aromatic hydrocarbons 2, the method of 2,2-trifluoroethyl thioether, is characterized in that: cuprous iodide, diimine, aromatic hydrocarbons halogen, sulphur powder, 2, the mol ratio of 2,2-trifluoro iodoethane and sodium borohydride is 0.1:0.2:1:2:2:3.
6. synthetic method according to claim 1, it is characterized in that: concrete steps are as follows: to adding cuprous iodide, diimine, aromatic hydrocarbons halogen, sulphur powder, 2 in the container of magnetic stirring apparatus, 2,2-trifluoro iodoethane, sodium borohydride and N, dinethylformamide, stopper is shut after mixing, put it in 80-95 DEG C of oil bath and continue to stir 1-24 hour, by extracted with diethyl ether, merge organic phase, with distilled water wash 3 times, organic phase anhydrous magnesium sulfate drying, filter, then revolve and steam removing organic solvent; The crude product obtained, by silica gel column chromatography, is that eluent carries out wash-out with Skellysolve A, obtains aromatic hydrocarbons 2,2,2-trifluoroethyl thioether.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232343A (en) * | 2018-10-24 | 2019-01-18 | 福州大学 | A kind of copper catalyzes and synthesizes aromatic hydrocarbons/alkane 2,2,2- trifluoroethyl selenide method and its application in insecticide |
| CN115160196A (en) * | 2022-06-30 | 2022-10-11 | 浙江大学衢州研究院 | Preparation method of symmetrical thioether compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104803898A (en) * | 2015-03-09 | 2015-07-29 | 华东师范大学 | Aryl-alkyl and aryl-aryl thioether compound and synthesis method thereof |
-
2016
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104803898A (en) * | 2015-03-09 | 2015-07-29 | 华东师范大学 | Aryl-alkyl and aryl-aryl thioether compound and synthesis method thereof |
Non-Patent Citations (3)
| Title |
|---|
| YONGWEN JIANG等: "A General and Efficient Approach to Aryl Thiols: CuI-Catalyzed Coupling of Aryl Iodides with Sulfur and Subsequent Reduction", 《ORGANIC LETTERS》 * |
| ZHENG-YU LONG等: "SRN1 reactions of 2,2,2-trifluoroethyl halides with thiolate ions", 《JOURNAL OF FLUORINE CHEMISTRY》 * |
| ZHIQIANG WENG等: "An Air-Stable Copper Reagent for Nucleophilic Trifluoromethylthiolation of Aryl Halides", 《ANGEW.CHEM.INT.ED.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232343A (en) * | 2018-10-24 | 2019-01-18 | 福州大学 | A kind of copper catalyzes and synthesizes aromatic hydrocarbons/alkane 2,2,2- trifluoroethyl selenide method and its application in insecticide |
| CN115160196A (en) * | 2022-06-30 | 2022-10-11 | 浙江大学衢州研究院 | Preparation method of symmetrical thioether compound |
| CN115160196B (en) * | 2022-06-30 | 2023-12-29 | 浙江大学衢州研究院 | Preparation method of symmetrical thioether compound |
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