CN104529850A - Method for preparing (Z) type tellurium-sulfur olefin compound - Google Patents

Method for preparing (Z) type tellurium-sulfur olefin compound Download PDF

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CN104529850A
CN104529850A CN201410820765.XA CN201410820765A CN104529850A CN 104529850 A CN104529850 A CN 104529850A CN 201410820765 A CN201410820765 A CN 201410820765A CN 104529850 A CN104529850 A CN 104529850A
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tellurium
thioether
phenyl
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clph
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邱仁华
陈锦杨
许新华
李宁波
王勰
何云华
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Hunan University
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Hunan University
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Abstract

The invention relates to a simple method for preparing a (Z) type asymmetrical tellurium-sulfur olefin compound conveniently. The tellurium and sulfur olefin compound is an important intermediate in organic synthesis and is also an important platform molecule for synthesis of a tri-substituted olefin compound and a tetra-substituted olefin compound. A terminal alkyne (as shown in the description) reacts with an asymmetric tellurium-sulfide ether (R<2>STeR<1>) under the catalysis of an inorganic alkali metal alkali or salt to produce the (Z) type tellurium-sulfur olefin compound highly stereo-selectively and region-selectively. The simple method provided for preparing the (Z) type tellurium-sulfur olefin compound has the advantages of mild reaction condition, simple experimental operation, high stereoselectivity and high yield. In addition, the method is convenient to operate and is suitable for industrial production, and the raw materials are low in cost and are readily available.

Description

The method of (Z) is prepared by one formula tellurium sulphur olefin(e) compound
[technical field]
The invention belongs to catalysis organic synthesis field, relate in particular to the synthetic method of one (Z) formula tellurium sulphur olefin(e) compound.
[background technology]
Tellurium sulphur olefin(e) compound is intermediate important in organic synthesis.(Z) formula tellurium sulphur olefin(e) compound owing to introducing the larger organic sulfur family atom (S, Te) of two reactive behavior difference simultaneously in same C-C double bond, C-S and the C-Te key at C-C double bond two ends is made to have different reactive behavioies, can be ruptured to C-S and C-Te key selectivity by diverse ways, introduce different groups simultaneously, thus obtain three, the four substituted olefine compounds with different replacements.A lot of natural product and medicine all have the configuration of three, four substituted olefines.Nearly ten years, domestic and international chemist has also carried out a large amount of report to the study on the synthesis of this dvitellurium sulfo-olefin(e) compound.But a lot of method is all faced with poor selectivity, operation difficulty, the defects such as productive rate is low.Therefore be badly in need of a kind of method easy and simple to handle, highly selective of exploitation and prepare this compounds.
Because Terminal Acetylenes hydrogen has certain acidity, under inorganic base metal alkali and salt catalysis, Terminal Acetylenes can with the reaction of asymmetric tellurium thia ether, obtain tellurium sulphur olefin(e) compound.Under the different inorganic base metal alkali of system thinking and salt condition, the situation of Terminal Acetylenes tellurium vulcanization reaction.Be intended to filter out a kind of efficient, cheap inorganic base metal catalyzer, high three-dimensional, regioselectivity ground preparation (Z) formula tellurium sulfo-olefin(e) compound.
[summary of the invention]
The object of the present invention is to provide a kind of method of easy preparation (Z) formula tellurium sulphur olefin(e) compound, to simplify experimental implementation, the productive rate improving target product and selectivity.
To achieve the above object of the invention, the present invention proposes following technical scheme:
A kind of method of synthesis (Z) formula tellurium sulphur olefin(e) compound makes reaction solvent, with Terminal Acetylenes with conventional organic solvent asymmetric tellurium thioether (R 2sTeR 1) be raw material, make catalyzer with inorganic base metal alkali or salt, after reaction terminates, obtain product (Z) formula tellurium sulphur olefin(e) compound through column chromatography.In above-mentioned synthetic method, described catalyst inorganic alkali metal base or salt are the one in lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, Quilonum Retard, sodium carbonate, salt of wormwood, cesium carbonate.
In above-mentioned synthetic method, described raw material Terminal Acetylenes preferred propargyl alcohol, 2-methyl fourth-3-alkynes-2-alcohol, 3-methoxyl group propine, 3-phenoxy group propine, 3-naphthyloxy propine, phenylacetylene, to methylbenzene acetylene, p-ethyl-phenylacetylene, to propylbenzene acetylene, to Methoxy-phenylacetylene, to chlorobenzene acetylene or to fluorobenzene acetylene.
In above-mentioned synthetic method, the asymmetric tellurium thioether of described raw material (R 2sTeR 1) preferred phenylbenzene tellurium thioether (R 1=Ph, R 2=Ph), phenyl n-propyl tellurium thioether (R 1=Ph, R 2=CH 3cH 2cH 2), phenyl (p-methylphenyl) tellurium thioether (R 1=Ph, R 2=p-MePh), phenyl (benzyl) tellurium thioether (R 1=Ph, R 2=CH 2ph), phenyl (rubigan) tellurium thioether (R 1=Ph, R 2=p-ClC 6h 4), phenyl (to propyl group) tellurium thioether (R 1=Ph, R 2=p-PrC 6h 4), phenyl (p-methoxyphenyl) tellurium thioether (R 1=Ph, R 2=p-MeOC 6h 4), phenyl (to fluorophenyl) tellurium thioether (R 1=Ph, R 2=p-FC 6h 4), (p-methylphenyl) phenyl tellurium thioether (R 1=p-MeC 6h 4, R 2=Ph), two (p-methylphenyl) tellurium thioether (R 1=p-MeC 6h 4, R 2=p-MeC 6h 4), (p-methylphenyl) (rubigan) tellurium thioether (R 1=p-MeC 6h 4, R 2=p-ClC 6h 4), (p-methylphenyl) (p-methoxyphenyl) tellurium thioether (R 1=p-MeC 6h 4, R 2=p-MeOC 6h 4), (rubigan) phenyl tellurium thioether (R 1=p-ClC 6h 4, R 2=Ph), two (rubigan) tellurium thioether (R 1=p-ClC 6h 4, R 2=p-ClC 6h 4), (rubigan) benzyl tellurium thioether (R 1=p-ClC 6h 4, R 2=CH 2ph), (rubigan) (p-methylphenyl) tellurium thioether (R 1=p-ClC 6h 4, R 2=p-MeC 6h 4).
In above-mentioned synthetic method, described solvent is the one in THF, methylene dichloride, toluene, acetonitrile, DMSO, DMF.
In above-mentioned synthetic method, mole addition of described catalyzer is 1.0-50%.In above-mentioned synthetic method, the condition of described catalyzed reaction is: at 0-50 DEG C, react 5-40 hour.
Synthetic method provided by the present invention is that the preparation of (Z) formula tellurium sulphur olefin(e) compound opens new low cost " green " approach, its advantage is: raw material sources are extensive, the selectivity of target product and productive rate are all higher, reaction conditions is gentle, operation is easy, and wide application range of substrates is general.
[accompanying drawing explanation]
The synthesis path figure of (Z) provided by the invention formula tellurium sulphur olefin(e) compound shown in Fig. 1.
[embodiment]
The synthesis path catalyzing and synthesizing (Z) formula tellurium sulphur olefin(e) compound method provided by the present invention, refers to accompanying drawing 1: by raw material Terminal Acetylenes asymmetric tellurium thioether (R 2sTeR 1) and catalyzer add in reaction vessel, add solvent, under the environment of 0-50 DEG C, react 5-40 hour under nitrogen protection, obtain target compound through column chromatography for separation.
Below in conjunction with concrete preparation example, the present invention will be further described:
preparation example 1
By 0.05mol lithium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL THF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 30h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 8%.
preparation example 2
By 0.05mol sodium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL THF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 30h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 14%.
preparation example 3
By 0.05mol potassium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL THF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 30h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 25%.
preparation example 4
By 0.05mol Quilonum Retard, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL THF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 30h.Reaction generates without expection product.
preparation example 5
By 0.05mol sodium carbonate, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL THF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 30h.Reaction generates without expection product.
preparation example 6
By 0.05mol salt of wormwood, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL THF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 30h.Reaction generates without expection product.
preparation example 7
By 0.05mol cesium carbonate, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL THF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 30h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 7.0%.
preparation example 8
By 0.05mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLTHF, under nitrogen protection, reaction at room temperature carries out 40h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 38%.
preparation example 9
By 0.05mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLDMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 40h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 41%.
preparation example 10
By 0.05mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL acetonitrile be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 40h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 34%.
preparation example 11
By 0.05mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL methylene dichloride be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 40h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 10%.
preparation example 12
By 0.05mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL toluene be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 40h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 15%.
preparation example 13
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 35h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 52%.
preparation example 14
By 0.15mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLDMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 27h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 67%.
preparation example 15
By 0.2mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLDMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 20h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 78%.
preparation example 16
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLDMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 78%.
preparation example 17
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 10h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 70%.
preparation example 18
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLDMF be placed in 50mL single port flask, under air atmosphere, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 28%.
preparation example 19
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLDMF be placed in 50mL single port flask, under nitrogen protection, react and carry out 15h at 0 DEG C.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 24%.
preparation example 20
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mLDMF be placed in 50mL single port flask, under nitrogen protection, react and carry out 15h at 50 DEG C.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-thiophenyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 54%.
preparation example 21
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenyl n-propyl tellurium thioether (R OH) 1=Ph, R 2=n-Pr) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain the positive rosickyite base third of (Z)-3-benzene telluro-2--2-alkene-1-alcohol through column chromatography for separation, productive rate is 78%.
preparation example 22
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenyl (p-methylphenyl) tellurium thioether (R OH) 1=Ph, R 2=p-MePh) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-to methylphenyl-sulfanyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 85%.
preparation example 23
By 0.1mol cesium hydroxide, 1.0mol propargyl alcohol (R=CH 2and 1.0mol phenyl (rubigan) tellurium thioether (R OH) 1=Ph, R 2=p-ClPh) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-3-benzene telluro-2-to chlorophenylsulfanyl third-2-alkene-1-alcohol through column chromatography for separation, productive rate is 84%.
preparation example 24
By 0.1mol cesium hydroxide, 1.0mol 2-methyl fourth-3-alkynes-2-alcohol (R=CH (CH 3) 2and 1.0mol phenylbenzene tellurium thioether (R OH) 1=Ph, R 2=Ph) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-2-methyl-3-thiophenyl-4-benzene telluro fourth-3-alkene-2-alcohol through column chromatography for separation, productive rate is 82%.
preparation example 25
By 0.1mol cesium hydroxide, 1.0mol 3-phenoxy group propine (R=CH 2and 1.0mol phenyl (rubigan) tellurium thioether (R OPh) 1=Ph, R 2=p-ClPh) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-1-benzene telluro-2-(to chlorophenylsulfanyl)-3-phenoxy group propylene through column chromatography for separation, productive rate is 91%.
preparation example 26
By 0.1mol cesium hydroxide, 1.0mol phenylacetylene and 1.0mol phenyl (rubigan) tellurium thioether (R 1=Ph, R 2=p-ClPh) and 20mL DMF be placed in 50mL single port flask, under nitrogen protection, reaction at room temperature carry out 15h.After reaction terminates, add suitable quantity of water, and be extracted with ethyl acetate, organic phase anhydrous Na 2sO 4drying, obtain (Z)-2-benzene telluro-1-(to chlorophenylsulfanyl) vinylbenzene through column chromatography for separation, productive rate is 90%.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.

Claims (5)

1. the method for synthesis (Z)-tellurium sulphur olefin(e) compound, it is characterized in that, catalyzer is made with the inorganic base metal alkali of catalytic amount or salt, with Terminal Acetylenes (R-≡) and asymmetric tellurium thioether (R2STeR1) for raw material, reaction solvent is made with conventional organic solvent, reaction is at room temperature effectively carried out, and obtain (Z)-tellurium sulphur olefin(e) compound, its structural formula is as follows high yield, highly-solid selectively:
2. synthetic method according to claim 1, is characterized in that, described catalyst inorganic alkali metal base or salt are the one in lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, Quilonum Retard, sodium carbonate, salt of wormwood, cesium carbonate.
3. synthetic method according to claim 1, it is characterized in that, described Terminal Acetylenes (R-≡) preferably propargyl alcohol, 2-methyl fourth-3-alkynes-2-alcohol, 3-methoxyl group propine, 3-phenoxy group propine, 3-naphthyloxy propine, phenylacetylene, to methylbenzene acetylene, p-ethyl-phenylacetylene, to propylbenzene acetylene, to Methoxy-phenylacetylene, to chlorobenzene acetylene or to fluorobenzene acetylene.
4. synthetic method according to claim 1, is characterized in that, the asymmetric tellurium thioether of described raw material (R 2sTeR 1) preferred phenylbenzene tellurium thioether (R 1=Ph, R 2=Ph), phenyl n-propyl tellurium thioether (R 1=Ph, R 2=CH 3cH 2cH 2), phenyl (p-methylphenyl) tellurium thioether (R 1=Ph, R 2=p-MePh), phenyl (benzyl) tellurium thioether (R 1=Ph, R 2=CH 2ph), phenyl (rubigan) tellurium thioether (R 1=Ph, R 2=p-ClPh), phenyl (to propyl group) tellurium thioether (R 1=Ph, R 2=p-prPh), phenyl (p-methoxyphenyl) tellurium thioether (R 1=Ph, R 2=p-MeOPh), phenyl (to fluorophenyl) tellurium thioether (R 1=Ph, R 2=p-FPh), (p-methylphenyl) phenyl tellurium thioether (R 1=p-MePh, R 2=Ph), two (p-methylphenyl) tellurium thioether (R 1=p-MePh, R 2=p-MePh), (p-methylphenyl) (rubigan) tellurium thioether (R 1=p-MePh, R 2=p-ClPh), (p-methylphenyl) (p-methoxyphenyl) tellurium thioether (R 1=p-MePh, R 2=p-MeOPh), (rubigan) phenyl tellurium thioether (R 1=p-ClPh, R 2=Ph), two (rubigan) tellurium thioether (R 1=p-ClPh, R 2=p-ClPh), (rubigan) benzyl tellurium thioether (R 1=p-ClPh, R 2=CH 2ph), (rubigan) (p-methylphenyl) tellurium thioether (R 1=p-ClPh, R 2=p-MePh).
5. synthetic method according to claim 1, is characterized in that, described solvent is the one in THF, methylene dichloride, toluene, acetonitrile, DMSO, DMF; Described reaction conditions is: at 0-50 DEG C, react 5-40 hour; The consumption of described catalyzer is 1.0%-50%.
CN201410820765.XA 2014-12-25 2014-12-25 Method for preparing (Z) type tellurium-sulfur olefin compound Pending CN104529850A (en)

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CN115260064A (en) * 2022-08-07 2022-11-01 湖南大学 Alkenyl thioether prepared by end alkyne high cis-selective hydrosulfide and synthetic method thereof
CN115260064B (en) * 2022-08-07 2023-10-20 湖南大学 Alkenyl thioether prepared by terminal alkyne high cis-form selective hydrosulfide and synthetic method thereof

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