CN106432002A - Synthesis method of 1,1,3-triphenyl-3-(o-chlorophenyl sulfonyl) propadiene - Google Patents
Synthesis method of 1,1,3-triphenyl-3-(o-chlorophenyl sulfonyl) propadiene Download PDFInfo
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Abstract
The invention relates to a synthesis method of 1,1,3-triphenyl-3-(o-chlorphenyl sulfonyl) propadiene as a following formula (which is shown in the description). The synthesis method comprises: in an organic solvent, under the presence of a composite catalyst, an oxidant, an assistant, alkali and an activating agent, a compound of a formula (I), a compound of a formula (II) and a compound of a formula (III) generate reaction, and after the reaction is completed, performing after-treatment, thereby obtaining a compound of a formula (IV), and all of the formulae are shown in the description. The synthesis method of the 1,1,3-triphenyl-3-(o-chlorphenyl sulfonyl) propadiene comprehensively cooperates and facilitates special reaction substrates and a catalytic reaction system, thereby achieving a purpose of facilitating high-efficiency transformation of materials; the compound can be obtained by a good product; technical conditions are tender; and wide market application prospect and industrial potential productivity are expressed.
Description
Technical field
The present invention relates to a kind of synthetic method of diene sulphonyl class compound, relate more particularly to 1,1,3- triphenyl -3-
The synthetic method of (Chloro-O-Phenyl sulfonyl) allene, belongs to organic chemical synthesis technical field.
Background technology
Diene class formation is the important synthesis precursor unit of many natural products and unnatural products, its unsaturation comprising
Double bond can carry out several functions modification, and purposes is quite varied, thus extensively should in conjugate addition and cycloaddition reaction
With this class formation not only shows efficient, single-minded reactivity, and sulphonyl class group also can be entered by elimination reaction
Row transformation.
Therefore, the high-efficiency synthesis method of exploitation dialkylene sulphonyl class compound causes the strongly emerging of numerous research workers
Interest.
Up to the present, the multiple synthesis sides about being related to dialkylene sulphonyl class compound have been occurred in that in prior art
Method, illustratively as follows：
(" the Cross-Coupling Reaction of Allenes with Aryl such as Fu Chunling
Halides.Synthesis of Polysubstituted 1,2-Allenyl Sulfones”,Or ganic Letters,
2005,7,1605-1607) report a kind of palladium chtalyst reacts preparation replacement allene base sulphonyl class compound with aryl halide
Method, its reaction equation is as follows：
Additionally, in recent years, about propiolic alcohol compound as synthon using also increasingly increasing, it is usually used in biology
Among the constructing of bioactive molecule, for example：
(" the Synthesis of Acrylonitriles through an FeCl3-Catalyz ed such as Hao Lu
Domino Propargylic Substitution/Aza-Meyer-Schuster Rearrangeme nt Sequence”,
Chem.Eur.J., 2012,18,6453-6456) report a kind of replacement of ferric trichloride catalytic, reset continuous reaction method,
Its reaction equation is as follows：
As above affiliated, disclose multiple synthetic methods of dialkylene sulphonyl class compound in prior art.However, existing two
The synthetic method of thiazolinyl sulphonyl class compound still can not meet the demand of organic chemical synthesis technical field.
The invention provides the synthetic method of 1,1,3- triphenyl -3- (Chloro-O-Phenyl sulfonyl) allene, the method is adopted
With three unique component reaction systems, and coordinate the structure of the reaction system especially catalyst system and catalyzing of uniqueness, and reach promotion
The purpose of material high-efficiency conversion, has successfully been obtained this compound with high yield, and process conditions are gentle, show extensive city
Field application prospect.
Content of the invention
In order to seek the synthetic method of dialkylene sulphonyl class compound, present inventor has performed in-depth study and exploration,
After having paid enough creative works, thus completing the present invention.
Specifically, technical scheme and content are related to a kind of following formula 1,1,3- triphenyl -3- (Chloro-O-Phenyl sulphur
Acyl group) allene synthetic method,
Methods described includes：Presence in organic solvent with composite catalyst, oxidant, auxiliary agent, alkali and activator
Under, lower formula (I) compound, formula (II) compound and formula (III) compound react, and react after terminating through post processing, thus
Obtain described formula (IV) compound,
In the described synthetic method of the present invention, described composite catalyst is mol ratio 1:1 organo-nickel compounds and ten
The mixture of dicarbapentaborane three-iron.
Wherein, described organo-nickel compounds are two (triphenylphosphine) Nickel dichloride. (NiCl2(PPh3)2), two (tricyclohexyl phosphines)
Nickel dichloride. (NiCl2(PCy3)2), double (1,5- cyclo-octadiene) nickel (Ni (COD)2) or nickel acetylacetonate (Ni (acac)2) in appoint
Meaning is a kind of, preferably two (tricyclohexyl phosphine) Nickel dichloride. (NiCl2(PCy3)2) or double (1,5- cyclo-octadiene) nickel (Ni (COD)2),
Most preferably two (tricyclohexyl phosphine) Nickel dichloride. (NiCl2(PCy3)2).
In the described synthetic method of the present invention, described oxidant is tert-butyl hydroperoxide (TBHP), 2- iodoxy benzene
Formic acid (IBX), double (trifluoroacetic acid) iodobenzene (PhI (TFA)2) or iodobenzene diacetate (PhI (OAc)2) in any one, optimum
Elect double (trifluoroacetic acid) iodobenzene (PhI (TFA) as2).
In the described synthetic method of the present invention, described auxiliary agent is trifluoromethanesulfonic acid cuprous (CuOTf).
In the described synthetic method of the present invention, described alkali is NaOH, potassium tert-butoxide, diethanolamine, 1,8- diaza two
Ring 11 carbon -7- alkene (DBU) or N, any one in N- dimethylethanolamine (DMEA), most preferably N, N- dimethyl ethanol
Amine (DMEA).
In the described synthetic method of the present invention, described organic solvent is DMF (DMF), dimethyl is sub-
Any one in sulfone (DMSO), benzene, acetonitrile, polyethylene glycol 200 (PEG-200) or 1,4- dioxane or arbitrarily multiple mixing
Compound, most preferably volume ratio 1:2 N,N-dimethylformamide (DMF) and the mixture of polyethylene glycol 200 (PEG-200).
Wherein, the consumption of described organic solvent does not have strict restriction, and those skilled in the art can be according to practical situation
Suitably selected and determined, to facilitate reaction to carry out and post processing, here is no longer carried out in detail such as its consumption size
Thin description.
In the described synthetic method of the present invention, described activator is hydroxy chloride ruthenium.
In the described synthetic method of the present invention, described formula (I) compound and formula (II) compound or formula (III) mole
Ratio is 1:1-2, for example, can be 1:1、1:1.5 or 1:2.
In the described synthetic method of the present invention, described formula (I) compound and composite catalyst (by organo-nickel compounds with
The total moles consumption sum meter of tri-iron dodecacarbonyl) mol ratio be 1:0.12-0.2, for example, can be 1:0.12、1:0.15、1:
0.18 or 1:0.2.
In the described synthetic method of the present invention, described formula (I) compound is 1 with the mol ratio of oxidant:1.5-2.5,
Can be for example 1:1.5、1:2 or 1:2.5.
In the described synthetic method of the present invention, described formula (I) compound is 1 with the mol ratio of auxiliary agent:0.08-0.14,
Can be for example 1:0.08、1:0.1、1:0.12 or 1:0.14.
In the described synthetic method of the present invention, described formula (I) compound is 1 with the mol ratio of alkali:1.2-1.8, for example
Can be 1:1.2、1:1.4、1:1.6 or 1:1.8.
In the described synthetic method of the present invention, described formula (I) compound is 1 with the mol ratio of activator:0.04-0.1,
Can be for example 1:0.04、1:0.06、1:0.08 or 1:0.1.
In the described synthetic method of the present invention, reaction temperature is 70-90 DEG C, for example, can be 70 DEG C, 80 DEG C or 90 DEG C.
In the described synthetic method of the present invention, the response time is 6-9 hour, for example, can be 6 hours, 7 hours, 8 hours
Or 9 hours.
In the described synthetic method of the present invention, the post processing after reaction terminates can be specific as follows：After reaction terminates, will be anti-
Answer liquid filtered while hot, the pH value adjusting filtrate, to neutral, is then fully washed with saturated aqueous common salt, add ethyl acetate extraction
2-3 time, merge organic faciess, anhydrous sodium sulfate drying, concentrating under reduced pressure, gained residue crosses silica gel column chromatography, with equal-volume ratio
The mixed liquor of acetone and petroleum ether carries out drip washing, thus obtaining described formula (IV) compound.
In sum, the invention provides a kind of synthesis of 1,1,3- triphenyl -3- (Chloro-O-Phenyl sulfonyl) allene
Method, methods described is worked in coordination with by the synthesis of specific reaction substrate and catalystic converter system and is promoted, thus having reached promotion
The purpose of material high-efficiency conversion, can obtain this compound by good product, and process conditions are gentle, show extensive city
Field application prospect and industrial production potential.
Specific embodiment
Below by specific embodiment, the present invention is described in detail, but the purposes of these exemplary embodiments and
Purpose is only used for enumerating the present invention, and not the real protection scope of the present invention is constituted with any type of any restriction, more non-general
Protection scope of the present invention is confined to this.
Wherein, in following all embodiments, the post processing after reaction terminates is all as follows：After reaction terminates, will react
Liquid filtered while hot, the pH value adjusting filtrate, to neutral, is then fully washed with saturated aqueous common salt, adds ethyl acetate extraction 2-
3 times, merge organic faciess, anhydrous sodium sulfate drying, concentrating under reduced pressure, gained residue crosses silica gel column chromatography, with the third of equal-volume ratio
The mixed liquor of ketone and petroleum ether carries out drip washing, thus obtaining described formula (IV) compound.
Embodiment 1
Under room temperature, to appropriate organic solvent (for volume ratio 1:2 N,N-dimethylformamide is mixed with polyethylene glycol 200
Compound) in, add formula (I) compound, 100mmol upper formula (II) compound, 200mmol upper formula (III) chemical combination on 100mmol
Thing, 12mmol composite catalyst (for the mixture of 6mmol bis- (tricyclohexyl phosphine) Nickel dichloride. and 6mmol tri-iron dodecacarbonyl),
Double (trifluoroacetic acid) iodobenzene (PhI (TFA) of 250mmol oxidant2), 8mmol auxiliary agent trifluoromethanesulfonic acid cuprous (CuOTf),
180mmol alkali N, N- dimethylethanolamine (DMEA) and 4mmol activator hydroxy chloride ruthenium, then stirring is warming up to 70 DEG C, and
Stirring reaction 9 hours at such a temperature；
After reaction terminates, post-treated, obtain formula (IV) compound, yield is 89.8%.
1H NMR(CDCl3,400MHz):δ8.16-8.13(m,1H),7.66-7.64(m,2H),7.37-7.28(m,
15H),7.19-7.15(m,1H).
Embodiment 2
, with embodiment 1, concrete course of reaction is as follows for reaction equation：
Under room temperature, to appropriate organic solvent (for volume ratio 1:2 N,N-dimethylformamide is mixed with polyethylene glycol 200
Compound) in, add formula (I) compound, 200mmol upper formula (II) compound, 100mmol upper formula (III) chemical combination on 100mmol
The thing, (mixing for 10mmol bis- (tricyclohexyl phosphine) Nickel dichloride. and 10mmol tri-iron dodecacarbonyl of 20mmol composite catalyst
Thing), double (trifluoroacetic acid) iodobenzene (PhI (TFA) of 150mmol oxidant2), 14mmol auxiliary agent trifluoromethanesulfonic acid cuprous (CuOTf),
120mmol alkali N, N- dimethylethanolamine (DMEA) and 10mmol activator hydroxy chloride ruthenium, then stirring is warming up to 90 DEG C, and
Stirring reaction 6 hours at such a temperature；
After reaction terminates, post-treated, obtain formula (IV) compound, yield is 89.4%.The same embodiment of characterize data
1.
Embodiment 3
Under room temperature, to appropriate organic solvent (for volume ratio 1:2 N,N-dimethylformamide is mixed with polyethylene glycol 200
Compound) in, add formula (I) compound, 130mmol upper formula (II) compound, 180mmol upper formula (III) chemical combination on 100mmol
Thing, 18mmol composite catalyst (for the mixture of 9mmol bis- (tricyclohexyl phosphine) Nickel dichloride. and 9mmol tri-iron dodecacarbonyl),
Double (trifluoroacetic acid) iodobenzene (PhI (TFA) of 220mmol oxidant2), 9mmol auxiliary agent trifluoromethanesulfonic acid cuprous (CuOTf),
170mmol alkali N, N- dimethylethanolamine (DMEA) and 8mmol activator hydroxy chloride ruthenium, then stirring is warming up to 75 DEG C, and
Stirring reaction 8 hours at such a temperature；
After reaction terminates, post-treated, obtain formula (IV) compound, yield is 89.5%.The same embodiment of characterize data
1.
Embodiment 4
Under room temperature, to appropriate organic solvent (for volume ratio 1:2 N,N-dimethylformamide is mixed with polyethylene glycol 200
Compound) in, add formula (I) compound, 150mmol upper formula (II) compound, 150mmol upper formula (III) chemical combination on 100mmol
Thing, 16mmol composite catalyst (for the mixture of 8mmol bis- (tricyclohexyl phosphine) Nickel dichloride. and 8mmol tri-iron dodecacarbonyl),
Double (trifluoroacetic acid) iodobenzene (PhI (TFA) of 200mmol oxidant2), 11mmol auxiliary agent trifluoromethanesulfonic acid cuprous (CuOTf),
150mmol alkali N, N- dimethylethanolamine (DMEA) and 7mmol activator hydroxy chloride ruthenium, then stirring is warming up to 80 DEG C, and
Stirring reaction 7 hours at such a temperature；
After reaction terminates, post-treated, obtain formula (IV) compound, yield is 90.1%.
Characterize data is with embodiment 1.
As can be seen here, the method for the present invention, can obtain purpose product with good yield, thus the conjunction for this compound
Become to provide brand-new synthetic method, there is good application potential and prospect.
Below, in order to investigate the impact of each factor, embodiment 1-4 has been carried out repeat to test, thus having investigated synthesis
The impact of each technical characteristic in reaction system.
Embodiment 5-24：The impact of composite catalyst component
Embodiment 5-8：Using two (triphenylphosphine) Nickel dichloride. (NiCl2(PPh3)2) replace two (tricyclohexyl phosphine) Nickel dichloride.
(NiCl2(PCy3)2), other operation all sames, thus repeating to implement embodiment 1-4, sequentially obtain embodiment 5-8.
Embodiment 9-12：Using double (1,5- cyclo-octadiene) nickel (Ni (COD)2) replace two (tricyclohexyl phosphine) Nickel dichloride.
(NiCl2(PCy3)2), other operation all sames, thus repeating to implement embodiment 1-4, sequentially obtain embodiment 9-12.
Embodiment 13-16：Using nickel acetylacetonate (Ni (acac)2) replace two (tricyclohexyl phosphine) Nickel dichloride. (NiCl2
(PCy3)2), other operation all sames, thus repeating to implement embodiment 1-4, sequentially obtain embodiment 13-16.
Embodiment 17-20：The one-component two (tricyclohexyl phosphine) the use of consumption being the total consumption sum of original two kinds of components
Nickel dichloride. (NiCl2(PCy3)2), other operation all sames, thus repeating to implement embodiment 1-4, sequentially obtain embodiment 17-
20.
Embodiment 21-24：The one-component tri-iron dodecacarbonyl the use of consumption being the total consumption sum of original two kinds of components, its
It operates all same, thus repeating to implement embodiment 1-4, sequentially obtains embodiment 21-24.
Result see table 1.
Table 1
As can be seen here：1st, when using other organo-nickel compounds, products collection efficiency is all led to significantly reduce；2nd, when only
During using two (tricyclohexyl phosphine) Nickel dichloride., yield reduction becomes apparent from；3rd, when simply using tri-iron dodecacarbonyl, yield is anxious
Sharp fall as little as 4.8-5.9%, has had been out any potentiality of industrialized production.In conjunction with above-described embodiment 17-20,21-24
Result visible, when simultaneously using two (tricyclohexyl phosphine) Nickel dichloride. (NiCl2(PCy3)2) with the mixture of tri-iron dodecacarbonyl
During as catalyst, create unexpected concerted catalysis effect between the two.
Embodiment 25-36：The impact of oxidant
Embodiment 25-28：Replace double (trifluoroacetic acid) iodobenzene (PhI (TFA) using tert-butyl hydroperoxide (TBHP)2),
Other operation all sames, thus repeating to implement embodiment 1-4, sequentially obtain embodiment 25-28.
Embodiment 29-32：Replace double (trifluoroacetic acid) iodobenzene (PhI (TFA) using 2- iodosobenzoic acid (IBX)2), its
It operates all same, thus repeating to implement embodiment 1-4, sequentially obtains embodiment 29-32.
Embodiment 33-36：Using iodobenzene diacetate (PhI (OAc)2) replace double (trifluoroacetic acid) iodobenzene (PhI (TFA)2),
Other operation all sames, thus repeating to implement embodiment 1-4, sequentially obtain embodiment 33-36.
Experimental result is as shown in table 2 below.
Table 2
As can be seen here, for oxidant, even with double (trifluoroacetic acid) iodobenzene (PhI (TFA)2) very similar two
Acetic acid iodobenzene (PhI (OAc)2), products collection efficiency also has obvious reduction, and other oxidant then reduces and becomes apparent from.This proves
The selection of oxidant is non-obvious.
Embodiment 37-40：The impact of auxiliary agent
In addition to dispensing cuprous for auxiliary agent trifluoromethanesulfonic acid therein (CuOTf), other operation all sames, thus repeat to grasp
Make embodiment 1-4, obtain embodiment 37-40.It was found that the products collection efficiency of embodiment 37-40 is 82.2-83.4%, phase
Embodiment 1-4 is significantly reduced, this proves the use of trifluoromethanesulfonic acid cuprous (CuOTf), can significantly improve reaction
Effect, improves products collection efficiency further.
Embodiment 41-56：The impact of alkali
Embodiment 41-44：Replace N, N- dimethylethanolamine using NaOH, other operation all sames, thus repeat to implement
Embodiment 1-4, sequentially obtains embodiment 41-44.
Embodiment 45-48：Replace N, N- dimethylethanolamine using potassium tert-butoxide, other operation all sames, thus repeat
Implement embodiment 1-4, sequentially obtain embodiment 45-48.
Embodiment 49-52：Replace N, N- dimethylethanolamine using diethanolamine, other operation all sames, thus repeat
Implement embodiment 1-4, sequentially obtain embodiment 49-52.
Embodiment 53-56：Replace N, N- dimethylethanolamine using 1,8- diazabicylo 11 carbon -7- alkene (DBU)),
Other operation all sames, thus repeating to implement embodiment 1-4, sequentially obtain embodiment 53-56.
Result see table 3.
Table 3
As can be seen here：In all of alkali, DMEA can have the effect organized, other alkali, especially highly basic such as NaOH
Or DBU, result in and more significantly reduced.
Embodiment 57-80：The impact of organic solvent
Embodiment 57-60：Using single solvent DMF (DMF), other operation all sames, thus repeat
Implement embodiment 1-4, sequentially obtain embodiment 57-60.
Embodiment 61-64：Using single solvent dimethyl sulfoxide (DMSO), other operation all sames, thus repeat to implement
Embodiment 1-4, sequentially obtains embodiment 61-64.
Embodiment 65-68：Using single solvent benzene, other operation all sames, thus repeating to implement embodiment 1-4, suitable
Secondary obtain embodiment 65-68.
Embodiment 69-72：Using single solvent acetonitrile, other operation all sames, thus repeating to implement embodiment 1-4,
Sequentially obtain embodiment 69-72.
Embodiment 73-76：Using single solvent polyethylene glycol 200 (PEG-200), other operation all sames, thus repeat
Implement embodiment 1-4, sequentially obtain embodiment 73-76.
Embodiment 77-80：Using single solvent Isosorbide-5-Nitrae-dioxane, other operation all sames, thus repeat to implement reality
Apply a 1-4, sequentially obtain embodiment 77-80.
Result see table 4.
Table 4
As can be seen here：When using any single organic solvent, yield is all significantly reduced, especially PEG-
200 and 1,4- dioxane reduce the most notable.But 1-4 is visible in conjunction with the embodiments, when the mixture using DMF and PEG-200
When, but achieve unexpected technique effect, this is unexpected.
Embodiment 81-84：The impact of activator
When being omitted activator hydroxy chloride ruthenium, other operation all sames, thus repeat to implement embodiment 1-
4, sequentially obtain embodiment 81-84.
Corresponding embodiment relation and products collection efficiency see table shown in 5.
Table 5
As can be seen here：When not using activator hydroxy chloride ruthenium, products collection efficiency is significantly reduced, and this proves hydroxy chloride
Change the use of ruthenium, can notable priming reaction process, thus significantly improving final effect.
In sum, the invention provides a kind of synthesis of 1,1,3- triphenyl -3- (Chloro-O-Phenyl sulfonyl) allene
Method, methods described is worked in coordination with by the synthesis of specific reaction substrate and catalystic converter system and is promoted, thus having reached promotion
The purpose of material high-efficiency conversion, can obtain this compound by good product, and process conditions are gentle, show extensive city
Field application prospect and industrial production potential.
It should be appreciated that the purposes of these embodiments is merely to illustrate the present invention and is not intended to limit the protection model of the present invention
Enclose.Additionally, it will also be appreciated that after the technology contents having read the present invention, those skilled in the art can make each to the present invention
Plant and change, change and/or modification, all these equivalent form of value equally falls within the guarantor that the application appended claims are limited
Within the scope of shield.
Claims (10)
1. a kind of synthetic method of following formula 1,1,3- triphenyl -3- (Chloro-O-Phenyl sulfonyl) allene,
Methods described includes：In organic solvent and in the presence of composite catalyst, oxidant, auxiliary agent, alkali and activator, under
Formula (I) compound, formula (II) compound and formula (III) compound react, and react after terminating through post processing, thus obtaining institute
State formula (IV) compound
2. synthetic method as claimed in claim 1 it is characterised in that：Described composite catalyst is mol ratio 1:1 organic nickel
Compound and the mixture of tri-iron dodecacarbonyl；
Wherein, described organo-nickel compounds are two (triphenylphosphine) Nickel dichloride. (NiCl2(PPh3)2), two (tricyclohexyl phosphine) chlorination
Nickel (NiCl2(PCy3)2), double (1,5- cyclo-octadiene) nickel (Ni (COD)2) or nickel acetylacetonate (Ni (acac)2) in any one
Kind, preferably two (tricyclohexyl phosphine) Nickel dichloride. (NiCl2(PCy3)2) or double (1,5- cyclo-octadiene) nickel (Ni (COD)2), optimum
Elect two (tricyclohexyl phosphine) Nickel dichloride. (NiCl as2(PCy3)2).
3. synthetic method as claimed in claim 1 or 2 it is characterised in that：Described oxidant is tert-butyl hydroperoxide
(TBHP), 2- iodosobenzoic acid (IBX), double (trifluoroacetic acid) iodobenzene (PhI (TFA)2) or iodobenzene diacetate (PhI (OAc)2)
In any one, most preferably double (trifluoroacetic acid) iodobenzene (PhI (TFA)2).
4. the synthetic method as described in any one of claim 1-3 it is characterised in that：Described auxiliary agent is that trifluoromethanesulfonic acid is cuprous
(CuOTf).
5. the synthetic method as described in any one of claim 1-4 it is characterised in that：Described alkali is NaOH, potassium tert-butoxide, diethyl
Hydramine, 1,8- diazabicylo 11 carbon -7- alkene (DBU) or N, any one in N- dimethylethanolamine (DMEA), optimum
Elect N, N- dimethylethanolamine (DMEA) as.
6. the synthetic method as described in any one of claim 1-5 it is characterised in that：Described activator is hydroxy chloride ruthenium.
7. the synthetic method as described in any one of claim 1-6 it is characterised in that：Described formula (I) compound is changed with formula (II)
The mol ratio of compound or formula (III) is 1:1-2.
8. the synthetic method as described in any one of claim 1-7 it is characterised in that：Described formula (I) compound and composite catalyzing
The mol ratio of agent is 1:0.12-0.2.
9. the synthetic method as described in any one of claim 1-8 it is characterised in that：Described formula (I) compound and oxidant
Mol ratio is 1:1.5-2.5.
10. the synthetic method as described in any one of claim 1-9 it is characterised in that：Described formula (I) compound is rubbed with auxiliary agent
That ratio is 1:0.08-0.14, and/or the mol ratio of described formula (I) compound and alkali is 1:1.2-1.8；And/or described formula (I)
Compound is 1 with the mol ratio of activator:0.04-0.1.
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| CHUNLING FU 等: "Cross-Coupling Reaction of Allenes with Aryl Halides，Synthesis of Polysubstituted 1 ,2-Allenyl Sulfones", 《ORGANIC LETTERS》 * |
| LU HAO 等: "Synthesis of Acrylonitriles through an FeCl3-Catalyzed Domino Propargylic Substitution/Aza-Meyer-Schuster Rearrangement Sequence", 《CHEMISTRY-A EUROPEAN JOURNAL》 * |
| ZHENG YANG 等: "Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides", 《THE JOURNAL OF ORGANIC CHEMISTRY》 * |
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