CN101343213B - Allyl ether series compound and preparation thereof - Google Patents

Allyl ether series compound and preparation thereof Download PDF

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CN101343213B
CN101343213B CN2008101202556A CN200810120255A CN101343213B CN 101343213 B CN101343213 B CN 101343213B CN 2008101202556 A CN2008101202556 A CN 2008101202556A CN 200810120255 A CN200810120255 A CN 200810120255A CN 101343213 B CN101343213 B CN 101343213B
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allyl ether
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CN101343213A (en
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崔冬梅
余科睿
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Zhejiang University of Technology ZJUT
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Abstract

The invention discloses a diallyl oxide compound as well as a preparation method thereof, the diallyl oxide compound has a structure as is shown in a formula (III), and R1 and R2 are respectively selected from hydrogen, and alkyl, phenyl and alkyl having 1 to 50 carbon atoms or phenyl, benzyl and nitrogenous heterocyclic residue substituted by alkoxy, and alkoxy having 1 to 50 carbon atoms independently in the formula (III). The preparation method is as follows: under the action of a transition metal catalyst M(PR3)X, an allene compound as shown in a formula (I) of the reactant and alcohol asshown in a formula (II) are in complete reaction when the temperature is controlled between 35 and 80 DEG C under the condition of presence of promoter protonic acid in an inert solvent, and the diallyl oxide compound shown in the formula (III) is obtained after the post treatment. The compound has broad application prospect, and the preparation method has advantages of mild reaction conditions, simple operation, high reaction yield, good selectivity, low pollution and good promotion and application prospect.

Description

Allyl ether series compound and preparation method thereof
(1) technical field
The present invention relates to allyl ether series compound and preparation method thereof.
(2) background technology
Allyl ether series compound is widely used in fields such as protecting group, polymer monomer or linking agent and photocuring, thermofixation, free radical curable coatings, air-drying property unsaturated polyester coating and flame-retarded resin as the important organic synthesis intermediate of a class.The synthetic method report of relevant allyl ether series compound is more, and for example traditional preparation method is by oxy-compound and allyl group halohydrocarbon condensation reaction synthetic (Liaoning chemical industry, 2001,30 (12), 531~532,552).But synthetic method commonly used can produce a large amount of by products, brings serious contaminate environment, does not also meet atom economy type principle.Therefore, invent a kind of efficient, economic synthetic method and seem very important.
(3) summary of the invention
The matter of utmost importance that the present invention will solve provides a class allyl ether series compound, described allyl ether series compound, and its structure is suc as formula shown in (III):
Figure G2008101202556D00011
In the formula (III), R 1, R 2Independently be selected from phenyl, benzyl, the nitrogen heterocyclic ring residue that hydrogen, the alkyl with 1~50 carbon atom, phenyl, alkyl or alkoxyl group replace, alkoxyl group separately with 1~50 carbon atom.
Further, described R 1Independently be selected from phenyl, to butyl phenyl, to amyl group phenyl or p-methoxyphenyl; R 2Independently be selected from the alkyl or the benzyl of 1~5 carbon atom.
Second technical problem that the present invention will solve provide a kind of reaction conditions gentleness, easy and simple to handle, reaction yield is high, selectivity good, pollutes less, has the allyl ether series compound preparation method of better popularizing application prospect.
For addressing the above problem, the preparation method of described allyl ether series compound is as follows: at transition-metal catalyst M (PR 3) under the effect of X, alcohol shown in propadiene compounds shown in the reactant formula (I) and the formula (II), controlled temperature fully reaction between 35~80 ℃ in inert solvent and under the promotor protonic acid existence condition, aftertreatment obtains the allyl ether series compound shown in the formula (III).Reaction equation is as follows:
Figure G2008101202556D00021
R in formula (I), the formula (II) 1, R 2Definition R in the cotype (III) respectively 1, R 2Definition, described alcohol can be primary alcohol (primary alconol), secondary alcohol (secondary alcohol) or tertiary alcohol (tertiary alcohol).
M (PR 3) among the X, M is Jinyang ion; PR 3For with the phosphine ligand of Jinyang ion coordination, wherein R 3Be phenyl or butyl; X is a negatively charged ion, and it is one of following that described X is selected from: cl anion, bromine anions, nitric acid negatively charged ion.
Further, the transition-metal catalyst described in the present invention preferably suc as formula (IV) expression nitric acid gold-triphenylphosphine complex compound;
(PPh 3)AuNO 3 (IV)
Reaction of the present invention needs to carry out under promotor protonic acid existence condition, generally adds the vitriol oil or methylsulfonic acid or trifluoromethanesulfonic acid, the preferred vitriol oil.
Described inert solvent is not for interfering the solvent of compound (I) and compound (II) reaction, its boiling point can be 60~250 ℃ of scopes, can be selected from halogenated hydrocarbon, substituted benzene or ether compound, specifically can select for use one of following: methylene dichloride, ethylene dichloride, toluene, chlorobenzene, ether, tetrahydrofuran (THF), dioxane.Be best as solvent wherein with ethers.
The present invention recommends to feed intake amount of substance than propadiene compounds (I): alcohol (II): M (PR 3) X: protonic acid=1:1.0~2.0:0.01~0.05:0.5~2.0.
The consumption of described inert solvent is: with respect to the propadiene compounds of every 1mol, use 0.5~1.0L.
The described reaction times is 2~10 hours.
Aftertreatment of the present invention can be adopted following steps: after reacting completely, dripping an amount of saturated sodium bicarbonate solution to solution does not have the bubble generation, adds water, and use ethyl acetate extraction, merge organic layer, drying, concentrate brown fraction, column chromatography gets the final product allyl ether series compound.
Concrete recommendation is described preparation method carry out according to following steps: under the condition of room temperature, add propadiene compounds (I) and inert solvent in the reactor, under condition of stirring, slowly add alcohol (II), add the nitric acid gold-triphenyl phosphorus complex compound (IV) and vitriol oil subsequently, finish intensification, reacted about 2~10 hours, treat that raw material reaction is complete, reduce to room temperature, dripping an amount of saturated sodium bicarbonate solution to solution does not have the bubble generation, adds water, and uses ethyl acetate extraction, merge organic layer, drying, concentrate brown fraction, column chromatography gets the final product allyl ether series compound.
The allyl ether series compound for preparing in view of the present invention is used in medicine industry field (Archives of Pharmacal Research.2001 as the important physical active substance, 24,271-276), simultaneously prepared allyl ether series compound can be further changes into the amino formate compounds (embodiment 22) of the allyl group replacement of widespread use in protein and polypeptide synthetic with the SULPHURYL CHLORIDE isocyanate reaction according to bibliographical information, therefore preparation method of the present invention has wide application prospect (Tetrahedron, 2001,57,8257-8266; Archives of Pharmacal Research.2001,24,271-276).
The preparation method of allyl ether series compound of the present invention, its key are to have selected for use auriferous compound to make catalyzer, and under the tart condition, reaction generates the compound with allyl ethers structure.Compared with prior art, its advantage is: (1) reaction conditions gentleness, easy to operate, product quality is good, the yield height.(2) to environment-friendly, the basic toxicological harmless of whole process of production produces, to operator also safety.(3) this reaction meets the atom economy principle, the raw material availability height.
(4) embodiment
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Embodiment 1:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00041
With propadiene base benzene (50mg, 0.338mmol), the vitriol oil (33.12mg, 18.0 μ l, 0.338mmol), nitro gold complex ((PPh) 3AuNO 3) (3.5mg, 0.00676mmol), (11.90mg, 15.1 μ l 0.372mmol) 1, mix in the 4-dioxane (1.5mL) methyl alcohol, and 6h is reacted in 70 ℃ of oil bath heating.Add saturated NaHCO 3The aqueous solution (1.0mL) is used ethyl acetate (10mL * 3) extraction then, uses anhydrous sodium sulfate drying, filters, and concentrates, and (sherwood oil: ethyl acetate=20:1), obtain target compound 46.2mg, yield is 72.4% to column chromatography, yellow oily liquid.
1HNMR(500MHz,CDCl 3):δ7.40~7.37(m,2H),7.33~7.29(m,2H),7.25~7.21(m,1H),6.61(d,J=16.0Hz,1H),6.28(dt,J=16.0,6.0Hz,1H),4.09(dd,J=6.0,1.5Hz,2H),3.39(s,3H).
Embodiment 2:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00051
Operation just replaces 1 with tetrahydrofuran (THF) with reference to embodiment 1, and the 4-dioxane obtains target product 40.0mg, and yield is 62.7%, the pale yellow oily liquid body.
Embodiment 3:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00052
Operation just replaces 1 with methylene dichloride with reference to embodiment 1, and the 4-dioxane obtains target product 10.0mg, and yield is 15.7%, the pale yellow oily liquid body.
Embodiment 4:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00061
Operation just replaces 1 with ethylene dichloride with reference to embodiment 1, and the 4-dioxane obtains target product 20.0mg, and yield is 31.3%, the pale yellow oily liquid body.
Embodiment 5:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00062
Operation just replaces 1 with chlorobenzene with reference to embodiment 1, and the 4-dioxane obtains target product 5.0mg, and yield is 7.8%, the pale yellow oily liquid body.
Embodiment 6:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00063
Operation just replaces the vitriol oil with trifluoromethanesulfonic acid with reference to embodiment 1, obtains target product 45.0mg, and yield is 70.5%, the pale yellow oily liquid body.
Embodiment 7:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00071
Operation just replaces the vitriol oil with methylsulfonic acid with reference to embodiment 1, obtains target product 43.0mg, and yield is 69%, the pale yellow oily liquid body.
Embodiment 8:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Operation is with reference to embodiment 1, and just methanol usage is that (23.80mg, 30.2 μ l 0.744mmol), obtain target product 46.0mg, and yield is 72%, the pale yellow oily liquid body.
Embodiment 9:
(E)-preparation of 1-(3-methoxyl group-1-propenyl) benzene:
Figure G2008101202556D00073
Operation is with reference to embodiment 1, and just temperature of reaction is a room temperature, obtains target product 3.0mg, and yield is 4.7%, the pale yellow oily liquid body.
Embodiment 10:
(E)-preparation of 1-(3-oxyethyl group-1-propenyl) benzene
Figure G2008101202556D00074
Operation just replaces methyl alcohol with ethanol with reference to embodiment 1, replaces 1 with tetrahydrofuran (THF), and the 4-dioxane obtains target product 43.0mg, and yield is 76.8%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.40~7.37(m,2H),7.32~7.28(m,2H),7.25~7.21(m,1H),6.60(d,J=16.0Hz,1H),6.30(dt,J=16.0,6.0Hz,1H),4.09(dd,J=6.0,1.5Hz,2H),3.55(q,J=7.0Hz,2H),1.25(t,J=7.0Hz,3H).
Embodiment 11:
(E)-preparation of 1-(3-isopropoxy-1-propenyl) benzene
Operation just replaces methyl alcohol with Virahol with reference to embodiment 1, obtains target product 45.4mg, and yield is 81%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.40~7.38(m,2H),7.38~7.28(m,2H),7.25~7.20(m,1H),6.60(d,J=16.0Hz,1H),6.30(dt,J=15.5,6.0Hz,1H),4.13(dd,J=6.0,1.5Hz,2H),3.70(m,1H),1.21(d,J=6Hz,6H).
Embodiment 12:
(E)-preparation of 1-(3-methoxyl group-1-propenyl)-4-anisole:
Figure G2008101202556D00082
Operation just replaces propadiene base benzene with 1-methoxyl group-4-propadiene base benzene with reference to embodiment 1, replaces 1 with toluene, and the 4-dioxane obtains target product 50.7mg, and yield is 83.2%, the pale yellow oily liquid body.
1HNMR(400MHz,CDCl 3):δ7.35-7.31(m,2H),6.88-6.83(m,2H),6.55(d,J=16.0Hz,1H),6.15(dt,J=16.0,6.4Hz,2H),4.07(dd,J=6.4,1.5Hz,2H),3.80(s,3H),3.38(s,3H).
Embodiment 13:
(E)-preparation of 1-(3-second methoxyl group-1-propenyl)-4-anisole:
Figure G2008101202556D00091
Operation just replaces propadiene base benzene with 1-methoxyl group-4-propadiene base benzene with reference to embodiment 1, and replaces methyl alcohol with ethanol, obtains target product 49.0mg, and yield is 74.5%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.33-7.31(m,2H),6.86-6.84(m,2H),6.55(d,J=16Hz,1H),6.17(dt,J=16,6.0Hz,2H),4.11(dd,J=6.0,1.0Hz,2H),3.81(s,3H),3.54(q,J=7.0Hz,2H),1.25(t,J=7.0Hz,3H)
Embodiment 14:
Figure G2008101202556D00092
Operation just replaces propadiene base benzene with 1-methoxyl group-4-propadiene base benzene with reference to embodiment 1, and replaces methyl alcohol with Virahol, obtains target product 57.3mg, and yield is 81.2%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.33-7.31(m,2H),6.85-6.83(m,2H),6.54?(d,J=15.5Hz,1H),6.17(dt,J=15.5,6.0Hz,2H),4.11(dd,J=6.0,1.5Hz,2H),3.0(s,3H),3.71-3.65(m,1H),1.20(d,J=6.0Hz,6H)
Embodiment 15:
(E)-preparation of 1-(3-benzyloxy-1-propenyl)-4-anisole:
Figure G2008101202556D00101
Operation just replaces propadiene base benzene with 1-methoxyl group-4-propadiene base benzene with reference to embodiment 1, and replaces methyl alcohol with phenylcarbinol, obtains target product 69.0mg, and yield is 79.3%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.38-7.29(m,7H),6.86-6.84(m,2H),6.57(d,J=16.0Hz,1H),6.20(dt,J=16.0,6.5Hz,2H),4.57(s,2H),4.17(dd,J=6.5,1.5Hz,3H),3.81(s,3H).
Embodiment 16:
(E)-preparation of 1-butyl-4-(3-methoxyl group-1-propenyl) benzene:
Operation just replaces propadiene base benzene with 1-butyl-4-propadiene base benzene with reference to embodiment 1, obtains target product 45.2mg, and yield is 82.7%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.29(d,J=8.0Hz,2H),7.12(d,J=8.0Hz,2H),6.57(d,J=16.0Hz,2H),6.23(dt,J=16.0,6.0Hz,1H),4.07(dd,J=6.0,1.5Hz,2H),3.37(s,3H),2.58(t,J=7.5Hz,2H),1.61-1.55(m,?2H),1.57-1.32(m,2H),0.92(t,J=7.5Hz,3H)
Embodiment 17:
(E)-preparation of 1-butyl-4-(3-isopropoxy-1-propenyl) benzene:
Figure G2008101202556D00111
Operation just replaces propadiene base benzene with 1-butyl-4-propadiene base benzene with reference to embodiment 1, and replaces methyl alcohol with Virahol, obtains target product 57.6mg, and yield is 85.4%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.29(d,J=8.5Hz,2H),7.12(d,J=8.5Hz,2H),6.57(d,J=16.0Hz,2H),6.25(dt,J=16.0,6.5Hz,1H),4.13(dd,J=6.5,1.5Hz,2H),3.71-3.65(m,1H),2.58(t,J=7.5Hz,2H),1.58-1.56(m,2H),1.35-1.29(m,2H),1.20(d,J=6.0Hz,6H),0.92(t,J=7.5Hz,3H)
Embodiment 18:
(E)-preparation of 1-butyl-4-(3-tertiary butyl Oxy-1-propenyl) benzene:
Figure G2008101202556D00112
Operation just replaces propadiene base benzene with 1-butyl-4-propadiene base benzene with reference to embodiment 1, and replaces methyl alcohol with the trimethyl carbinol, obtains target product 60.5mg, and yield is 84.6%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.29(d,J=8.0Hz,2H),7.10(d,J=8.0Hz,?2H),6.57(d,J=16.0Hz,2H),6.25(dt,J=16.0,6.0Hz,1H),4.06(dd,J=6.0,1.5Hz,2H),2.58(t,J=7.5Hz,2H),1.61-1.54(m,2H),1.36-1.31(m,2H),0.92(t,J=7.2Hz,3H)
Embodiment 19:
(E)-preparation of 1-(3-methoxyl group-1-propenyl)-4-amylbenzene:
Operation just replaces propadiene base benzene with 1-amyl group-4-propadiene base benzene with reference to embodiment 1, obtains target product 53.9mg, and yield is 93.1%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.30(d,J=8.5Hz,2H),7.12(d,J=8.5Hz,2H),6.57(d,J=16.0Hz,2H),6.23(dt,J=16.0,6.0Hz,1H),4.06(dd,J=6.0,1.5Hz,2H),3.37(s,3H),2.57(t,J=7.5Hz,2H),1.63-1.56(m,2H),1.34-1.29(m,4H),0.88(t,J=7.0Hz,3H)
Embodiment 20:
(E)-preparation of 1-(3-oxyethyl group-1-propenyl)-4-amylbenzene:
Operation just replaces propadiene base benzene with 1-amyl group-4-propadiene base benzene with reference to embodiment 1, and replaces methyl alcohol with ethanol, obtains target product 60.8mg, yield〉99%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.29(d,J=8.0Hz,2H),7.10(d,J=8.0Hz,?2H),6.57(d,J=16.0Hz,2H),6.25(dt,J=16.0,6.0Hz,1H),4.11(dd,J=6.0,1.5Hz,2H),3.53(q,J=7.0Hz,2H),2.57(t,J=7.5Hz,2H),1.63-1.56(m,2H),1.33-1.30(m,4H),1.24(t,J=7.0Hz,3H),0.88(t,J=7.0Hz,3H)
Embodiment 21:
(E)-preparation of 1-(3-isopropoxy-1-propenyl)-4-amylbenzene:
Figure G2008101202556D00131
Operation just replaces propadiene base benzene with 1-amyl group-4-propadiene base benzene with reference to embodiment 1, and replaces methyl alcohol with Virahol, obtains target product 60.3mg, and yield is 93%, the pale yellow oily liquid body.
1HNMR(500MHz,CDCl 3):δ7.29(d,J=8.0Hz,2H),7.11(d,J=8.0Hz,2H),6.57(d,J=15.5Hz,2H),6.25(dt,J=15.5,6.0Hz,1H),4.12(dd,J=6.0,1.5Hz,2H),3.71-3.65(m,1H),2.57(t,J=7.5Hz,2H),1.63-1.58(m,2H),1.34-1.29(m,4H),1.20(d,J=6.0Hz,6H),0.88(t,J=7.0Hz,3H)。
Embodiment 22:
Figure G2008101202556D00132
In the time of 20 ℃; under nitrogen protection; in order yellow soda ash (0.7155g; 6.75mmol), SULPHURYL CHLORIDE isocyanic ester (0.64g; 4.5mmol), (E)-1-(3-isopropoxy-1-propenyl) benzene (0.528g; 3mmol) join in the anhydrous methylene chloride, stir, and temperature is controlled at about 20 ℃.With the liquid phase monitoring,, add H in the reaction process until reacting completely 2O (10mL) termination reaction with ethyl acetate extraction (10mL * 2), merges organic layer.The sodium sulfite solution of adding 25% and 10% potassium hydroxide solution in organic layer, stirred overnight at room temperature, anhydrous magnesium sulfate drying is used in organic layer saturated common salt water washing afterwards, concentrates.Enriched material is crossed post, uses ethyl acetate drip washing, finally obtains the shielded N-cinnamyl group-carbamic acid isopropyl ester of N, i.e. product B, yield 76%.

Claims (8)

1. the preparation method of an allyl ether series compound is characterized in that described preparation method is as follows: at transition-metal catalyst M (PR 3) under the effect of X, alcohol shown in propadiene compounds shown in the reactant formula (I) and the formula (II), controlled temperature fully reaction between 35~80 ℃ in inert solvent and under the promotor protonic acid existence condition, aftertreatment obtains the allyl ether series compound shown in the formula (III); Described inert solvent is selected from halogenated hydrocarbon, substituted benzene or ether compound; It is one of following that described promotor protonic acid is selected from: the vitriol oil, methylsulfonic acid or trifluoromethanesulfonic acid;
In formula (I), formula (II) or the formula (III), R 1Be selected from hydrogen, have the alkyl, phenyl of 1~50 carbon atom, to butyl phenyl, to amyl group phenyl, p-methoxyphenyl, benzyl, have the alkoxyl group of 1~50 carbon atom; R 2Be selected from alkyl, phenyl, the benzyl with 1~50 carbon atom, alkoxyl group with 1~50 carbon atom;
M (PR 3) among the X, M is Jinyang ion; PR 3For with the phosphine ligand of Jinyang ion coordination, wherein R 3Be phenyl; X is a negatively charged ion, and it is one of following that described X is selected from: cl anion, bromine anions, nitric acid negatively charged ion.
2. the preparation method of allyl ether series compound as claimed in claim 1 is characterized in that described transition-metal catalyst is the nitric acid gold-triphenylphosphine complex compound suc as formula (IV) expression;
(PPh 3)AuNO 3 (IV)。
3. the preparation method of allyl ether series compound as claimed in claim 1, it is one of following to it is characterized in that described inert solvent is selected from: methylene dichloride, ethylene dichloride, toluene, chlorobenzene, ether, tetrahydrofuran (THF), dioxane.
4. as the preparation method of the described allyl ether series compound of one of claim 1~3, the amount of substance that it is characterized in that feeding intake is than propadiene compounds (I): alcohol (II): M (PR 3) X: protonic acid=1: 1.0~2.0: 0.01~0.05: 0.5~2.0.
5. the preparation method of allyl ether series compound as claimed in claim 4 is characterized in that the consumption of described inert solvent is: with respect to the propadiene compounds of every 1mol, use 0.5~1.0L.
6. the preparation method of allyl ether series compound as claimed in claim 1 is characterized in that the described reaction times is 2~10 hours.
7. the preparation method of allyl ether series compound as claimed in claim 1, it is characterized in that described aftertreatment employing following steps: after reacting completely, drip an amount of saturated sodium bicarbonate solution to solution and do not have the bubble generation, add water, and use ethyl acetate extraction, merge organic layer, drying, concentrate brown fraction, column chromatography gets the final product allyl ether series compound.
8. the preparation method of allyl ether series compound as claimed in claim 1 is characterized in that described R 1Independently be selected from phenyl, to butyl phenyl, to amyl group phenyl or p-methoxyphenyl; R 2Independently be selected from the alkyl or the benzyl of 1~5 carbon atom.
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Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
Berthiol, Florian
Berthiol, Florian;et al..Heck reaction of protected allyl alcohols with aryl bromides catalyzed by a tetraphosphanepalladium complex.European Journal of Organic Chemistry.2005,(7),1367-1377. *
difference in mechanism between hydroalkoxylation and hydroamination.Tetrahedron Letters.2008,
difference in mechanism between hydroalkoxylation and hydroamination.Tetrahedron Letters.2008,49(33),4908-4911.
et al..Heck reaction of protected allyl alcohols with aryl bromides catalyzed by a tetraphosphanepalladium complex.European Journal of Organic Chemistry.2005,(7),1367-1377.
Nishina, Naoko
Nishina, Naoko;Yamamoto, Yoshinori.Gold-catalyzed intermolecular hydroalkoxylation of allenes difference in mechanism between hydroalkoxylation and hydroamination.Tetrahedron Letters.2008, difference in mechanism between hydroalkoxylation and hydroamination.Tetrahedron Letters.2008,49(33),4908-4911. *
Yamamoto, Yoshinori.Gold-catalyzed intermolecular hydroalkoxylation of allenes

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