CN104058910A - Method for synthesizing triphenylethylene compounds under synergic catalytic action of chlorobenzene and palladium - Google Patents
Method for synthesizing triphenylethylene compounds under synergic catalytic action of chlorobenzene and palladium Download PDFInfo
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Abstract
The invention discloses a method for synthesizing triphenylethylene compounds under synergic catalytic action of chlorobenzene and palladium, which comprises the following steps: by taking iodo-substituted aromatic hydrocarbon and aryl alkyne as substrates and tris(dibenzylideneacetone)dipalladium as a catalyst precursor, under synergic catalytic action of chlorobenzene, reacting the iodo-substituted aromatic hydrocarbon and the aryl alkyne to generate the triphenylethylene compounds in one step. According to the invention, the method is simple to operate and low in cost; the addition of a traditional phosphine ligand is not needed in the reaction; and in the reaction process, less catalyst is consumed, the reaction product yield is high, and the atom economy is high.
Description
Technical field
The invention belongs to the synthesis technical field of triphenylethylene compounds, be specifically related to chlorobenzene as crucial additive, promote palladium catalysis cascade reaction to prepare the method for triphenylethylene compounds.
Background technology
The chemical compound lot that includes triphenyl thylene structure unit has very important medicine and pharmacology function, and it to have large conjugated structure be the important intermediate structure of constructing luminescent material.In pharmaceutical chemistry field, it can be used as selective estrogen receptor modulators or as the important component part of the traction group of cancer therapy drug, the important drugs as TAM or OHT as treatment mammary cancer.Ethylene linkage in the structural unit of triphenylethylene has transmission electronic effect, and its distinctive structure can be eliminated π-π stacking and concentration quenching, promotes to form amorphous film, makes it at aspects such as luminous organic materials, have extensive application.The synthetic two large class methods that mainly contain around triphenyl thylene structure unit, one class is to take traditional alkene building-up reactions as basic synthetic triphenylethylene compounds, the use that the method is a large amount of to the Grignard reagent of air-sensitive or phosphorus ylide reagent etc., such as people such as Xu Jiarui, utilize wittig-horner reaction, utilize diaryl ketone and phosphorus ylide reagent synthetic triphenylethylene derivative under the condition of THF and potassium tert.-butoxide, use difficult synthetic, expensive phosphorus ylide reagent and special substrate diaryl ketone, and used stronger alkali potassium tert.-butoxide.Another kind of is to utilize palladium, rhodium, the carbon carbon cross-coupling that nickel etc. are transition metal-catalyzed or alkynes virtue hydrogenation synthesize triphenylethylene conjugated body, Shi Zhangjie group is by 1, the two aromatic hydrocarbons acetylene of 1-and the synthetic triphenylethylene of iodo aromatic ring one step Heck coupling, He Chenwanzhi group of Mao Jincheng group utilizes 1-aromatic hydrocarbons-2, the Suzuki coupling of the two bromine alkene of 2-and continuous two steps of aryl boric acid, synthetic triphenyl thylene structure unit, He Wuhuayue group of Robbins group utilizes respectively nickel catalysis chlorinated aromatic hydrocarbons and tolane, palladium catalysis aryl boric acid and tolane, through Hydroarylation, reaction generates triphenylethylene.Although transition metal-catalyzed synthetic method can avoid using Grignard reagent, the phosphorus ylide of air-sensitive mostly, but these react the special starting raw material of general Structure of need and comparatively complicated part, substrate suitability is bad, severe reaction conditions, have limited existing transition metal-catalyzed widespread use in triphenylethylene is synthetic.
Summary of the invention
Technical problem to be solved by this invention is to overcome the shortcoming that existing triphenylethylene compounds preparation method exists, the method of one-step synthesis triphenylethylene compounds is provided, the method is used three (dibenzalacetone) two palladiums and chlorobenzene concerted catalysis, do not adding under the condition of part, one step synthesizes triphenylethylene compounds by iodo aromatic hydrocarbons and arylalkyne, simple to operate, reaction conditions is gentle, and Atom economy is high.
Solving the problems of the technologies described above adopted technical scheme is: under protection of inert gas; iodo aromatic hydrocarbons, arylalkyne, salt of wormwood, three (dibenzalacetone) two palladiums, chlorobenzene are added in absolute ethanol; wherein the mol ratio of iodo aromatic hydrocarbons and arylalkyne, salt of wormwood is 3～4:1:2～3; the add-on of three (dibenzalacetone) two palladiums is 4%～6% of arylalkyne molar weights; the add-on of chlorobenzene is 1～4 times of three (dibenzalacetone) two palladium molar weights; 60～80 ℃ are reacted 2～12 hours, obtain triphenylethylene compounds.
The mol ratio of the preferred iodo aromatic hydrocarbons of the present invention and arylalkyne, salt of wormwood be the add-on of 3:1:2, three (dibenzalacetone) two palladiums be arylalkyne molar weight 5%, the add-on of chlorobenzene is 2 times of three (dibenzalacetone) two palladium molar weights.
Above-mentioned iodo aromatic hydrocarbons is specifically selected
in formula, R represents H, CH
3, CH
3any one in O, Br; Arylalkyne is specifically selected
in formula, R represents H, CH
3, CH
3o, CH
3cH
2, any one in Br.
It is substrate that iodo aromatic hydrocarbons and arylalkyne are take in the present invention, and collaborative three (dibenzalacetone) the two palladium catalytic iodine of chlorobenzene generate triphenylethylene compounds for aromatic hydrocarbons and arylalkyne one step.The present invention is simple to operate, and reaction is without adding traditional poisonous phosphine part, and in reaction process, catalyzer usage quantity is few, reaction product yield is high, and Atom economy is high.
Embodiment
Below in conjunction with embodiment, the present invention is described in more detail, but invention which is intended to be protected is not limited only to these embodiment.
Embodiment 1
Take that to prepare the following triphenylethylene of structural formula be example, raw materials used and preparation method thereof be:
Under nitrogen protection; 0.0114g (0.025mmol) three (dibenzalacetone) two palladiums and 0.138g (1mmol) salt of wormwood are added in Shrek pipe; vacuumize logical nitrogen three times; then add 55 μ L (0.5mmol) phenylacetylenes, 172 μ L (1.5mmol) iodobenzenes, 5 μ L (0.05mmol) chlorobenzenes, 5mL absolute ethanol; at 70 ℃, stir 2 hours; stopped reaction; drop to room temperature; filtration obtains thick product; then column chromatography is separated; obtain white solid triphenylethylene, its yield is 80%.Products therefrom characterizes with Bruker Avance type superconduction fourier numeralization nuclear magnetic resonance spectrometer, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.25-7.14 (m, 8H), 7.10 (dd, 2H), 7.04-6.97 (m, 3H), 6.93 (d, 2H), 6.86 (s, 1H);
13c NMR (101MHz, CDCl
3) δ: 143.43,142.60,140.37,137.39,130.38,129.54,128.61,128.19,128.16,127.95,127.60,127.49,127.39,126.73.
Embodiment 2
With prepare structural formula following 1,1 ', 2-tri-(4-methyl-phenyl) ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced methylbenzene acetylene with equimolar, and iodobenzene is replaced methyl iodobenzene with equimolar, other steps are identical with embodiment 1, are prepared into white oily matter 1,1 ', 2-tri-(4-methyl-phenyl) ethene, its productive rate is 50%, characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.20 (d, 2H), 7.10 (dd, 6H), 6.92 (s, 4H), 6.86 (s, 1H), 2.36 (s, 3H), 2.33 (s, 3H), 2.24 (s, 3H);
13c NMR (101MHz, CDCl
3) δ: 140.56,140.00,136.65,136.02,135.81,135.20,133.81,129.22,128.35,128.26,127.81,127.62,126.43,126.05,20.27,20.11,20.06.
Embodiment 3
With prepare structural formula following 1,1 ', 2-tri-(3-methyl-phenyl) ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced with equimolar methylbenzene acetylene, and iodobenzene is replaced with equimolar methyl iodobenzene, other steps are identical with embodiment 1, are prepared into white solid 1,1 ', 2-tri-(3-methyl-phenyl) ethene, its productive rate is 51%, characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.29 (dd, 3H), 7.20 (dd, 3H), 7.14-7.05 (m, 3H), 6.99 (t, 3H), 6.88 (d, 1H), 2.41 (d, 6H), 2.28 (s, 3H);
13c NMR (101MHz, CDCl
3) δ: 142.60,141.58,139.44,137.05,136.61,136.34,136.24,129.72,129.48,127.36,127.13,126.99,126.70,126.36,125.40,123.80,20.43,20.33,20.27.
Embodiment 4
With prepare structural formula following 1,1 ', 2-tri-(4-methoxyl group-phenyl) ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced anisole acetylene with equimolar, iodobenzene is replaced methoxyl group iodobenzene with equimolar, other steps are identical with embodiment 1, be prepared into yellow solid 1,1 ', 2-tri-(4-methoxyl group-phenyl) ethene, its productive rate is 72%, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.18-7.15 (m, 2H), 7.07-7.02 (m, 2H), 6.90 (t, 2H), 6.81-6.74 (m, 4H), 6.70 (s, 1H), 6.62-6.57 (m, 2H), 3.75 (s, 3H), 3.73 (s, 3H), 3.67 (s, 3H);
13c NMR (101MHz, CDCl
3) δ ppm:158.03,157.82,157.08,138.85,135.63,130.58,129.57,127.62,124.75,113.04,112.53,112.40,54.28,54.18,54.12.
Embodiment 5
With prepare structural formula following 1,1 ', 2-tri-(the bromo-phenyl of 4-) ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced bromobenzene acetylene with equimolar, and iodobenzene is replaced bromo-iodobenzene with equimolar, other steps are identical with embodiment 1, are prepared into white solid 1,1 ', 2-tri-(the bromo-phenyl of 4-) ethene, its productive rate is 40%, characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.44 (dd, 4H), 7.27 (d, 2H), 7.13 (d, 2H), 7.02 (d, 2H), 6.89 (s, 1H), 6.86 (d, 2H);
13cNMR (101MHz, CDCl
3) δ: 140.52,140.08,137.29,134.62,131.04,130.40,129.97,128.15,126.73,121.06,120.13.
Embodiment 6
To prepare the following 1-of structural formula (4-aminomethyl phenyl)-1 ', 2-diphenylethlene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced methylbenzene acetylene with equimolar, and other steps are identical with embodiment 1, be prepared into white oily mater 1-(4-aminomethyl phenyl)-1 ', 2-diphenylethlene, its productive rate is 52%, isomery ratio is 50/50, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.28 (d, 15H), 7.23 (d, 2H), 7.15-7.01 (m, 9H), 6.92 (d, 6H), 2.35 (s, 3H), 2.23 (s, 3H);
13cNMR (101MHz, CDCl
3) δ: 142.48,141.55,140.63,139.54,136.52,136.26,136.00,135.49,133.47,129.33,129.23,128.47,128.42,128.28,127.66,127.59,127.12,127.10,126.89,126.62,126.46,126.38,126.28,126.25,125.59,20.27,20.11.
Embodiment 7
To prepare the following 1-of structural formula (4-ethylphenyl)-1 ', 2-diphenylethlene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced with equimolar p-ethyl-phenylacetylene, and other steps are identical with embodiment 1, be prepared into white oily solid 1-(4-ethylphenyl)-1 ', 2-diphenylethlene, its productive rate is 70%, isomery ratio is 50/50, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.26-7.09 (m, 15H), 7.07-6.94 (m, 8H), 6.86 (s, 4H), 6.83 (s, 1H), 2.58 (q, 2H), 2.46 (q, 2H), 1.16 (d, 3H), 1.08 (t, 3H);
13c NMR (101MHz, CDCl
3) δ: 142.68,142.51,142.36,141.88,141.61,140.60,139.57,136.54,136.45,133.69,129.32,129.24,128.48,127.61,127.12,127.10,127.01,126.88,126.63,126.45,126.37,126.27,125.57,27.58,27.46,14.37,14.25.
Embodiment 8
To prepare the following 1-of structural formula (4-p-methoxy-phenyl)-1 ', 2-diphenylethlene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced anisole acetylene with equimolar, and other steps are identical with embodiment 1, be prepared into white oily solid 1-(4-p-methoxy-phenyl)-1 ', 2-diphenylethlene, its productive rate is 65%, isomery ratio is 50/50, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.37-7.28 (m, 10H), 7.26-7.14 (m, 5H), 7.11 (dt, 5H), 7.06 (d, 2H), 6.94 (d, 2H), 6.91 (s, 1H), 6.89 (s, 1H), 6.84 (d, 2H), 6.65 (d, 2H), 3.80 (s, 3H), 3.71 (s, 3H);
13c NMR (101MHz, CDCl
3) δ: 157.93,157.35,142.80,142.56,141.23,139.63,139.56,136.63,131.51,130.59,129.76,129.38,129.03,128.47,127.67,127.12,126.94,126.78,126.68,126.63,126.43,126.36,126.23,126.15,125.56,112.97,112.38,54.14,54.08.
Embodiment 9
With prepare structural formula following 1,2-bis-(3-aminomethyl phenyl)-1 '-phenyl ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, iodobenzene used is replaced with equimolar methyl iodobenzene, and other steps are identical with embodiment 1, be prepared into white oily solid 1,2-bis-(3-aminomethyl phenyl)-1 '-phenyl ethene, its productive rate is 52%, isomery ratio is 50/50, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.34-7.28 (m, 3H), 7.01t, 19H), 6.91 (s, 3H), 6.84 (s, 1H), 6.78 (d, 1H), 2.31 (d, 8H), 2.17 (s, 3H);
13c NMR (101MHz, CDCl
3) δ: 142.56,142.45,141.78,141.48,139.54,139.31,137.14,136.67,136.45,136.31,129.76,129.46,129.32,128.47,127.50,127.41,127.21,127.18,127.12,127.05,126.87,126.74,126.42,126.36,126.25,125.59,125.46,123.80,123.83,20.45,20.37,20.29.
Embodiment 10
With prepare structural formula following 1,2-bis-(3-aminomethyl phenyl)-1 '-(4-aminomethyl phenyl) ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced methylbenzene acetylene with equimolar, iodobenzene used is replaced with equimolar methyl iodobenzene, other steps are identical with embodiment 1, be prepared into white oily solid 1,2-bis-(3-aminomethyl phenyl)-1 '-(4-aminomethyl phenyl) ethene, its productive rate is 52%, isomery ratio is 50/50, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.20 (dd, 2H), 7.18 (s, 1H), 7.15 (d, 2H), 7.13-7.05 (m, 9H), 7.03-6.94 (m, 4H), 6.91 (d, 4H), 6.88 (d, 3H), 6.79 (d, 1H), 2.37 (s, 3H), 2.31 (s, 6H), 2.29 (s, 3H), 2.25 (s, 3H), 2.18 (s, 3H);
13cNMR (101MHz, CDCl
3) δ: 142.75,142.66,141.50,140.83,139.53,137.16,136.63,136.50,136.45,136.31,135.89,135.40,133.58,129.74,129.51,129.20,128.38,128.18,127.63,127.42,127.24,127.14,127.05,126.98,126.90,126.80,126.71,126.33,125.35,123.87,123.73,20.45,20.44,20.39,20.31,20.28,20.12.
Embodiment 11
With prepare structural formula following 1,2-bis-(4-aminomethyl phenyl)-1 '-(4-p-methoxy-phenyl) ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced anisole acetylene with equimolar, iodobenzene used is replaced methyl iodobenzene with equimolar, other steps are identical with embodiment 1, be prepared into white oily solid 1,2-bis-(4-aminomethyl phenyl)-1 '-(4-p-methoxy-phenyl) ethene, its productive rate is 48%, isomery ratio is 50/50, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.16-7.10 (m, 4H), 7.07-6.99 (m, 10H), 6.88 (d, 2H), 6.86 (s, 2H), 6.84 (s, 1H), 6.76 (dd, 4H), 6.59 (d, 2H), 3.74 (s, 2H), 3.71 (s, 1H), 3.65 (s, 3H), 2.30 (s, 4H), 2.26 (s, 5H), 2.18 (s, 3H);
13c NMR (101MHz, CDCl
3) δ: 158.05,157.81,157.17,140.19,140.09,140.04,139.48,136.68,136.09,135.90,135.78,135.44,135.19,133.87,131.88,130.54,129.65,129.36,129.24,128.34,128.27,127.81,127.64,126.47,126.31,125.95,125.59,125.23,112.94,112.49,112.34,54.25,54.15,54.09,20.29,20.13,20.07.
Embodiment 12
With prepare structural formula following 1,2-bis-(3-aminomethyl phenyl)-1 '-(4-p-methoxy-phenyl) ethene is example, raw materials used and preparation method thereof is:
In embodiment 1, phenylacetylene used is replaced anisole acetylene with equimolar, iodobenzene used is replaced with equimolar methyl iodobenzene, other steps are identical with embodiment 1, be prepared into white oily solid 1,2-bis-(3-aminomethyl phenyl)-1 '-(4-p-methoxy-phenyl) ethene, its productive rate is 62%, isomery ratio is 50/50, and characterization data is:
1h NMR (400MHz, CDCl
3) δ: 7.25-6.97 (m, 17H), 6.94 (d, 2H), 6.90 (d, 2H), 6.88-6.79 (m, 5H), 6.66 (d, 2H), 3.81 (s, 3H), 3.72 (s, 3H), 2.31 (d, 3H), 2.19 (s, 3H);
13c NMR (101MHz, CDCl
3) δ: 157.88,157.28,142.87,142.71,141.15,139.75,139.59,137.22,136.60,136.34,131.73,130.56,129.78,129.71,129.47,129.16,127.49,127.33,127.17,126.98,126.92,126.77,126.36,126.29,125.36,123.91,123.63,112.87,112.33,54.15,54.08,20.45,20.43,20.40,20.34.
Claims (3)
1. the triphenylethylene compounds synthetic method of the collaborative palladium catalysis of a chlorobenzene; it is characterized in that: under protection of inert gas; iodo aromatic hydrocarbons, arylalkyne, salt of wormwood, three (dibenzalacetone) two palladiums, chlorobenzene are added in absolute ethanol; wherein the mol ratio of iodo aromatic hydrocarbons and arylalkyne, salt of wormwood is 3～4:1:2～3; the add-on of three (dibenzalacetone) two palladiums is 4%～6% of arylalkyne molar weights; the add-on of chlorobenzene is 1～4 times of three (dibenzalacetone) two palladium molar weights; 60～80 ℃ are reacted 2～12 hours, obtain triphenylethylene compounds.
2. chlorobenzene according to claim 1 is worked in coordination with the triphenylethylene compounds synthetic method of palladium catalysis, it is characterized in that: the mol ratio of described iodo aromatic hydrocarbons and arylalkyne, salt of wormwood is 3:1:2, the add-on of three (dibenzalacetone) two palladiums is 5% of arylalkyne molar weights, and the add-on of chlorobenzene is 2 times of three (dibenzalacetone) two palladium molar weights.
3. the triphenylethylene compounds synthetic method of the collaborative palladium catalysis of chlorobenzene according to claim 1 and 2, is characterized in that: described iodo aromatic hydrocarbons is
in formula, R represents H, CH
3, CH
3any one in O, Br; Described arylalkyne is
in formula, R represents H, CH
3, CH
3o, CH
3cH
2, any one in Br.
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| CN108424346A (en) * | 2018-03-21 | 2018-08-21 | 中山大学 | Three halogens replace triphenylethylene class photochromic material and its synthetic method and application |
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| EP1167372A1 (en) * | 2000-06-28 | 2002-01-02 | Takasago International Corporation | 2,2-(Diaryl)vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst |
| US7642391B1 (en) * | 2005-03-04 | 2010-01-05 | Iowa State University Research Foundation, Inc. | Palladium-catalyzed coupling of aryl halides with alkynes |
| CN102381916A (en) * | 2011-08-22 | 2012-03-21 | 浙江大学 | Synthesis method of beta, beta-diaryl alkene |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1167372A1 (en) * | 2000-06-28 | 2002-01-02 | Takasago International Corporation | 2,2-(Diaryl)vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst |
| EP1167372B1 (en) * | 2000-06-28 | 2003-12-10 | Takasago International Corporation | 2,2-(Diaryl)vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst |
| US7642391B1 (en) * | 2005-03-04 | 2010-01-05 | Iowa State University Research Foundation, Inc. | Palladium-catalyzed coupling of aryl halides with alkynes |
| CN102381916A (en) * | 2011-08-22 | 2012-03-21 | 浙江大学 | Synthesis method of beta, beta-diaryl alkene |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108424346A (en) * | 2018-03-21 | 2018-08-21 | 中山大学 | Three halogens replace triphenylethylene class photochromic material and its synthetic method and application |
| CN108424346B (en) * | 2018-03-21 | 2021-06-11 | 中山大学 | Trihalo-substituted triphenylethylene photochromic material and synthesis method and application thereof |
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